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Bobby’s Bike Hike offers Chicago’s top rated walking tours designed to help you better orientate yourself, learn interesting stories, and meet amazing folks from all over the globe.  Our entertaining guides set the standard and make sure your experience is top notch.


  • Chicago Favorites Food Tour

    11:30am Tues, Thurs, Sat, Sun

    Sample your way through Chicago’s most popular food scene.  Enjoy Chicago-style pizza and hot dogs, craft beers, and indulge in a brownie from the folks who invented it.  This walking tour shows you some of the most beautiful sites in downtown Chicago from Millennium Park to the lobby of the...

    Learn MoreChicago Cultural Center
    SCHEDULE
    11:30am Tues, Thurs, Sat, Sun
    LEVEL
    Totally Walkable
    DURATION
    3 hours
    LENGTH
    1.5 miles
    PRICE

    Adults
    $48.75
    Students/Military/Seniors
    $43.75

     

    Adult
    $48.75
    Student / Military
    $43.75
    Students / Seniors 65+
    Kids under 12
    Kids under 4
    Highlights
    Chicago Loop
    Chicago Style Pizza
    Millennium Park
    Famous Chicago-mix popcorn
    Locally Crafted Beer
    Chicago-style Hot Dog
    State Street (that Great Street)
    Crown Fountain
    Cloud Gate
    Chicago Cultural Center
    The Original Brownie
    Custom Line
    11:30am Tues, Thurs, Sat, Sun
    Map Graphic
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    Private Group Request
    PRICE
    Starting at: $43.75
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  • Chinatown Food & Culture Walking Tour

    4pm Friday & Saturday

    Discover the delicious and multi-regional cuisine of China without leaving Chicago on Bobby’s Chinatown Food Tour.  We’ll explore the complex layers of Chinese culture and the many contributions these people have made to both Chicago and the World.  And what better way to show off Chin...

    Learn MorePui Tak Center
    SCHEDULE
    4pm Fri & Sat
    LEVEL
    Very Easy
    DURATION
    2.5 hrs
    LENGTH
    1 mile
    PRICE

    Adults
    $48.75
    Students/Military/Seniors
    $43.75
    Kids (under 4)
    $10.00

     

    Adult
    $48.75
    Student / Military
    $43.75
    Students / Seniors 65+
    $43.75
    Kids under 12
    Kids under 4
    Highlights
    Wentworth Avenue
    Dim Sum Treats
    Egg Tarts
    Lamb & Cumin Sandwich
    Chinese Cultural Institution
    Hot Pots
    Hot Tea
    Beijing Duck
    Custom Line
    4pm Friday & Saturday
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    Reserve Now
    Private Group Request
    PRICE
    Starting at $43.75
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  • Chicago River Walking Tour

    9am Saturdays

    From hosting Chicago’s first inhabitants to reversing its flow to the transportation of today, the Chicago River is the life-blood of this great City.  We’ll explore the history of the Chicago River, it’s many bridges, as well as sample some of the many eateries that have brough...

    Learn More
    SCHEDULE
    9am Saturdays
    LEVEL
    Easy
    DURATION
    1.5 hours
    LENGTH
    1 mile
    PRICE

    Adults
    $25.00
    Students/Military/Seniors
    $20.00
    Kids (under 12)
    $15.00
    Kids (under 4)
    $5.00

    Adult
    $25.00
    Student / Military
    $20.00
    Students / Seniors 65+
    $20.00
    Kids under 12
    Kids under 4
    Highlights
    Chicago Riverwalk
    Amazing Architecture
    Wrigley Building
    Vietnam Memorial & Park
    McCormick Bridge house and River Museum
    Centennial Fountain & Water Arc
    Gorgeous Bridges
    Chicago’s Lakefront
    Custom Line
    9am Saturdays
    Map Graphic
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    Private Group Request
    PRICE
    Starting at $15
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  • Sweets & Spirits Dessert Walking Tour

    Private Groups Only

    What could be better than fun drinks and delicious desserts in the River North area?  Sip and sample your way through many tasty treats like chocolates and cakes and try fantastic cocktails unique to Chicago!   Share fun stories about Chicago’s history with friends (21 and older, please) whi...

    Learn MoreChicago Cultural Center
    SCHEDULE
    Private Groups Only
    LEVEL
    Easy
    DURATION
    2.5 hours
    LENGTH
    1 mile
    PRICE

    Adults
    $46.75
    Students/Military/Seniors
    $41.75

     

    Adult
    $46.75
    Student / Military
    $41.75
    Students / Seniors 65+
    $41.75
    Kids under 12
    Kids under 4
    Highlights
    Michigan Avenue
    Decadent Treats
    River North Nightlife
    Trendy Cocktails
    Local Chocolates
    Dylan’s Candy Store
    Fun, Fun, Fun
    Custom Line
    Private Groups Only
    Reserve Now
    Map Graphic
    https://www.bobbysbikehike.com/wp-content/uploads/2017/01/Chicago-Favorites-Walking.jpg
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    Private Group Request
    PRICE
    Starting at: $41.75
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  • Chicago Craft Beer-Tasting Tour

    Private Groups Only

    What is Chicago’s favorite past time?  Baseball maybe?  Politics?  Ice fishing on Lake Michigan?  Nope, it’s beer brewing.  Chicago has so many high quality big and small brewers within it’s city limits that there is good reason that the City’s residents spend most of th...

    Learn MoreChicago Cultural Center
    SCHEDULE
    Private Groups Only
    LEVEL
    Easy
    DURATION
    2.5 hours
    LENGTH
    1 mile
    PRICE

    Adults
    $46.75
    Students/Military/Seniors
    $42.75

     

    Adult
    $46.75
    Student / Military
    Students / Seniors 65+
    Kids under 12
    Kids under 4
    Highlights
    Amazing Neighborhoods
    Hidden Pubs
    Well-known Chicago hangouts
    Pilsners
    India Pale Ales
    Belgium Blonds
    Custom Line
    Private Groups Only
    Reserve Now
    Map Graphic
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    Private Group Request
    PRICE
    Starting at $42.75
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Why book a Chicago Walking Tour?

Bobby’s Bike Hike offers a wide variety of award-winning Chicago city walking tours and consistently ranks as having the top tours in Chicago.  Plus, we’re proud to be Chicago’s largest and most popular walking tour company, offering new and unique tours each and every year.

Why are walking tours so popular in Chicago?  Good Question.  And we have the answer.  Chicago is consistently ranked one of the country’s top walkable cities because of its flat terrain, ease of use, and abundance of wide sidewalks and pathways.  You can safely and easily walk anywhere in Chicago without fear of fatigue, and many of Chicago’s top activities and attractions are within relatively close walking distance of each other.  Plus, to top it off residents of Chicago are incredibly friendly.  Midwestern charm is real folks, and you can witness it first hand as we walk through this amazing City.

Our sole purpose is to educate, entertain and help in anyway we can! Please feel free to call 312-245-9300 with questions, ideas, or comments. You may also contact us using this email form.

Bobby's Bike Hike Lake Shore Drive & Ohio Street 540 N. Lake Shore Drive Chicago, Illinois 60611 312-245-9300
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Chicago Favorites: Food & Walking Tour Chicago River Walking Tour Chinatown Food & Culture Walking Tour Sweets & Spirits Dessert Walking Tour Chicago Craft Beer-Tasting Walking Tour
LEVEL Mostly Easy Ridiculously Easy  Very Easy Amazingly Easy Refreshingly Easy
DURATION 3 hours 1.5 hours 2.5 hours 2.5 hours 2.5 hours
LENGTH 1.5mi/2.4km 1mi/1.6km 1mi/1.6km 1mi/1.6km 1mi/1.6km
PRICE Adults
$48.75
Stu/Mil/Sen65+
$43.75
Adults
$25.00
Stu/Mil/Sen65+
$20.00
Kids under 12
$15.00
Kids under 4
$5.00
Adults
$48.75
Stu/Mil/Sen65+
$43.75
Kids under 4
$10.00
Adults
$46.75
Stu/Mil/Sen65+
$41.75
Adults
$46.75
Stu/Mil/Sen65+
$41.75
STARTING POINT Chicago Cultural Center
77 E. Randolph Street
Chicago Riverwalk Pui Tak Center
2216 S. Wentworth
Downtown Chicago
Michigan Avenue
Various Neighborhoods
CLOSEST “L” TRAIN Red Line: Lake Stop Blue Line: Clark/Lake
Purple/Brown Line: Merchandise Mart
Red Line: Cermak-Chinatown Stop Red Line: Grand Stop TBD
ENDING POINT 226 S. Wabash DuSable Harbor Pui Tak Center TBD TBD
CAPACITY 16 people 16 people 16 people 16 people 16 people
KID FRIENDLY  No Yes Yes No No
PRIVATE GROUP TOUR Yes  Yes Yes Yes Yes
FOOD OFFERED  Yes  No  Yes  Yes, snacks  No
AGE REQUIREMENT  Yes, 16 and Older  No  No  Yes, 21 and older  Yes, 21 and older

Walking Tours Frequently Asked Questions

“Strenuous” is not in Bobby’s vocabulary. All of Bobby’s walking tours are set at a relaxed to moderate pace for walkers of all skill levels. Our guides will lead you from attraction to attraction, stopping to give you insight into this amazing City. At many landmarks, there will be places to sit down during the presentation. And of course, on our Food & Walking Tours we will stop and sit at each Chicago restaurant that we visit.

We CAN provide food substitutions for vegetarians on ALL tours. Gluten-free substitutions are available on certain tours. While we try our very best to accommodate food allergies, we cannot guarantee certain avoidance from various food allergies. We would encourage you to ask questions along the way and see if our guide might recommend a substitution.

Sorry, we do not allow pets on any of our tours. Actually, you can bring a goldfish in a plastic bag. Actually, no don’t bring the goldfish either.

Our walking tours start at various locations around the City and while we do our best to accommodate restrooms at the start of your tour, we do highly recommend using the restroom prior to arrival to your tour. We will have restroom stops built in to each walking tour. For our food and walking tours, all of the restaurants we visit will have restrooms to use.

We change the tour slightly every six to eight months. Many parts of the tour remain the same, but we do our best to improve upon and enhance the tour. Don’t be embarrassed to come back for more and repeat the experience – many people do! We had one guest tell us he has taken the same tour 8 different times. When we mentioned he should look at one of the many other tours we offered, he stated no need. His reason is every time he takes the same tour he gets a different tour guide and each tour guide provides their own unique spin and presentation style. So if you come back to the same tour, be prepared for a new and engaging experience each and every time.

Absolutely! Many of our attendees live right here in Chicago or the outlying suburbs. Locals often attend to learn things about the neighborhoods and the city in which they live that they did not know beforehand. We mainly stay off the beaten path, and thus avoid being consumed by crowds. Locals (and those that want to feel like locals) can often get the MOST out of the tours since the tours are designed to show you how the locals live, work, eat, and play in each neighborhood we cover.

We do not provide water on our tours due to the fact that they all originate from locations outside of our headquarters. Please plan ahead and bring water with you. For our culinary, restaurant and food tours our restaurant partners will provide water free of charge.

All of our tours at the present moment do allow for ADA compliant and wheelchair accessible. But please note that sometimes our restaurants change and we cannot guarantee every restaurant will not include stairs of some sort which might make things difficult. But a majority of our stops should be ADA compliant.

No stroller, no problem! We rent strollers out for daily use, multi-daily use. But most of our walking tours do not originate from our bike shop. So you will want to make arrangements in advance to rent and pick up your stroller. Please note that our tour guides many times meets the group directly in the neighborhood covered on the tour, without stopping at the bike shop, so we cannot deliver strollers to you.

You should wear clothes, of course, but beyond that you’re free to show your expressive nature in what you decide to wear. We recommend you bring small items such as an ID, credit card and cash (to tip the guide), cell phone, and camera.

We suggest tennis shoes and comfortable, loose-fitting clothes that are appropriate for the weather conditions on the day of your tour. We strongly suggest you wear layers, particularly in spring and fall, as you can always take a layer off if you get too hot or add a layer if you get too cool. Many of our tours are downtown, close to Lake Michigan, which is one of the largest lakes in the world and can alter the temperature quickly based on the direction of the wind.

15 people per tour is the perfect number for most of our walking tours.

Our walking and cultural tours have been developed for a wide variety of ages, interests, and skill levels. So you’ll want to pick the tour that is appropriate for you and your group. Regarding seniors, we rarely hear that seniors have a hard time on our tours as long as they feel comfortable walking. Seniors might want to beware of taking the tour in extreme temperatures. Regarding kids on our tours, not every tour is appropriate for younger hikers. For instance, we do not recommend our Chicago Favorites Walking & Food Tour for participants under the ages of 17 due to the fact that we do go into bars on this particular tour. That said, we do realize that every child is different so we do leave it in the hands of the parents to ultimately decide what is ok for their child and what is not. It might be that you just sit outside during the stops that include the bar. A good rule of thumb to know whether a tour is kid-friendly to see if we offer kid prices on the tour. If no kid prices, it’s probably not the best suited. But again, it’s up to the parents to ultimately decide because all kids are different. Whether to bring your child is ultimately up to your discretion, but please note that ALL CHILDREN need a paid ticket. For food tours, we assume that if your child is below age 3 than they will not be participating in the food tasting portion of the tour or that they might be sharing food with a parent. Therefore, for children below age 3, no ticket is required and there will not be a food portion dedicated to this child. If you’d like food for your child under 3, then please do purchase a ticket in advance. Either way, please indicate when you sign up whether you are bringing a child on the tour so that our tour guide can be prepared. We do rent strollers should you need them. If your child becomes unruly we would just ask that you step away from the group for a bit to calm your child down before returning to the group.

Not more than you can handle! The pace is usually good for everyone. We’ve rated each tour level so that you can pick the right tour for you. We do stop at various points of interest and attractions so that you can have a brief rest while our tour guides explain the history of Chicago in a way that brings the stories to life. While you want to make sure the distance we cover is suitable for you, remember that we will never be walking continuously for that amount of time. We will have 6-8 stops mixed in along the route for resting periods and to learn about Chicago. Please note that with some of our walking tours there are some stairs that we navigate during the tour.

Expect the very best. Our staff takes great pride in being the best in their field. So we do not skimp on any of the details. All of our tours are different and they all go in various directions around the City. Our staff has spent a lot of time and energy making sure that we bring the very best of Chicago to you on our tours. So each route is carefully detailed and every story is crafted to perfection to make sure you come away with the best Chicago experience possible. Our walking tours allow for a much more intimate experience with the neighborhoods, foods, and cultures that we visit.

Our walking tours are led by experienced Award-winning Bobby’s Bike Hike tour guides. During our tours you will learn about the history and culture of the various neighborhoods and attractions we visit, as well as get to see Chicago the way Chicagoans experience their City. Bobby’s Bike Hike is one of the most popular City Tour companies in the country, offering quality tours since 2002. We are proud to have put walking tours on the map in Chicago! Bobby’s Bike Hike Tours is a mid-sized local tour business that concentrates on details, organization, and accuracy. We will not show you anything unless we know about, believe in it, and love it! We use old school methods, modern technology, and a lot of personality with everything that we do. We focus on good honest food and fun, striving to make sure each person that takes our tours has a memorable Chicago experience.

Explorers, Culture Lovers, Friends, Family, and everyday people too! Our walking tours are designed for anyone that loves exploring great neighborhoods, top attractions, and lesser known highlights while listening to interesting stories about the history and culture that make Chicago a world class city. We have so many walking tours to choose from including ones appropriate to explore unique neighborhoods, the foods that made Chicago famous, Chicago Culinary & Culture tours, Chicago’s gangster history, and kid-friendly side to Chicago.

 

Buying Tickets

Why would you want to cancel? Don’t worry: if there is an unforeseen change in your schedule, you can cancel your tour with 72 hour notice. There is a 10% processing fee for any cancellations.

Bike tours are offered from March through November because these are the months you can usually rely on good Chicago weather, while walking tours are offered year-round.  Tours do run rain or shine, and you should always dress appropriately for the day’s weather conditions.  Note that Chicagoland is huge, so when they predict “scattered showers” it probably won’t affect the tour.  We provide free ponchos on our bike tours when the weather requires, and on walking tours it’s usually easy to duck inside (or stay inside) for a moment until a shower passes.   In the rare event that a tour is canceled due to extreme weather, we will allow you to reschedule your tour (subject to availability) or offer a full refund.

There is a minimum number of people needed for our tours to go out.  Although solo customers can always sign up and join our tour, we do require at least two participants for any of our bike tours to go out.  And we require a minimum of three participants in order for any of our Food Tours to go out.  If we do not meet or exceed that number within 2 hours of tour time you might be contacted and could be asked to either reschedule, be offered a Gift Certificate for future tour, or cancel all together (with full refund).

It’s always a beautiful day at Bobby’s Bike Hike and we strongly suggest you dress for the weather, preferably in layers.  We run most of our tours in any type of weather.  Our Bike Tour season is scheduled during months when the weather is predicted to be good, so our schedule reflects that.  We ride in rain but will usually cancel a tour if lighting is present at the start of the tour.  We keep a close watch on the sky and we may decide to start a tour a little late or might cancel all together.  In the rare occurrence that we cancel a tour due to weather we’ll offer you a substitute tour at a different time or day, or offer a full refund for your missed tour.  We do provide ponchos if there happens to be a brief shower while out on the bike tour.  Our walking tours run year round as they are less dependent on stable weather for their operation.  During the nicer months, we use the beautiful outdoor promenades for our walking tours.  And during inclement weather we can duck down and use Chicago’s unique underground pedway system to get from point to point. Just remember to always dress for the weather.  Because our walking tours do not leave from our headquarter location, we do not provide rain ponchos should a pop up shower occurs

We accommodate all sorts of groups.  We have performed an incredible experience many times over for Girl Scout troops, Boy scouts, bachelor and bachelorette parties, school groups, family reunions, college alumni rides, sorority and fraternity mixers, seniors, bike clubs, corporate retreats, teambuilding outings and countless others.  Because of the diversity of our tour selection, we can cater our tours to any type of group.  Email us or give us a call.

There is a standard cost to book a private tour. We can accommodate from 1-300 people. If you book well in advance there is a good chance that we can accommodate your needs. We have both biking and walking tours and you can add food to any of our tours.  To inquire about a private tour, please fill out the form you’ll find on any of our main tour pages (Bike, Walking, or Food) or you can find the form on each individual tour page.  Our Director of Group Fun will contact you within 24 hours to inform you if the date and time requested is available, and answer any of your questions.  If you need immediate answers you can call our main number 312.245.9300 and select option 2.

Yes, gift certificates are available for all Bobby’s Bike Hike guided tours and rentals.  And they make a perfect gift for holidays, birthdays or any other occasion! To purchase a gift certificate, please click on the “SHOP/SERVICE” link on our Menu.  We can ship them to you or to a friend/family member.

Bobby’s Bike Hike does not include gratuities in the cost of our tours. A standard gratuity for a tour guide in Chicago is 18% to 20% of the tour price. If you had a great time gratuities are accepted by our tour guides. We do not provide ATM’s at any of our locations, so please plan ahead and bring cash with you to tip your guide for a job well done.

Yes, Yes, Yes, Yes, and Yes.  We offer discounts for students and military who must bring a valid ID.  We can tell if you’re a high school student so you won’t need anything to prove there, but college students should bring their college ID cards.  Same with military personnel, we give you discounts because we appreciate what you do for our country.  We just ask that you bring your military ID in order to receive the discount.  Seniors, we appreciate you to.  Any seniors 65 and older receive discounts as well.  The travel agent discount is our Student/Military/Senior Ticket rate. Please reserve online to receive this discount, you’ll save an additional 10% by booking online.  We will ask that you supply a business card at the time of your tour to retain the discount.  Kid prices are substantially discounted on our tours, whether your child is under 12 or under 4.  All kids will need a ticket.  And all of our online prices are 10% off our in-shop rates.  So make sure to book in advance for discounts and to guarantee your space on the tour.

We do not officially provide a waiting list. If a date is sold out, there is always a chance that we will add an additional tour. Please email us or call us (312) 933.2980 and let us know what date you are interested in.

We strongly encourage you purchase tour tickets in advance. We have been giving tours since 2002 and often sell out quickly (especially on the weekends). Saturdays are the busiest day of the week! You don’t want to get caught at the last minute so check out our tour schedule and availability. Booking ahead guarantees your space on our tour, plus saves you 10%.

Our Chicago Guided Tour tickets are sold by calling 312.245.9300 or by reserving online through our website. We work with a third party software that handles our online ticket sales so we can spend more time doing what we do best, creating the best bike, walking, & food tours available. Tickets can be purchased online or over the phone with a Visa, Mastercard, or American Express. Checks and Travelers Checks are not accepted.

 

About Bobby’s Bike Hike

Bobby’s Bike Hike was founded in 2002 by Jeremy L, a then 27 year old ambitious (and slightly naive) newcomer to the Chicago tourism scene. He named the business Bobby’s Bike Hike as a tribute to his late father Bob, a bus tour operator in Arkansas who instilled Jeremy’s passion for travel and the tourism industry. Jeremy’s interest in healthy living and a clean environment inspired him to create an interactive bike tour that would let people truly experience the city he loved. Today, Jeremy continues to deliver on his father’s advice to never focus on being the biggest, only on being the BEST!

Yes, we do have bathrooms available. But because our bathroom can be in high demand, we strongly encourage that you use the restroom prior to your arrival to our bike shop. Many of our walking tours start at various locations around the City so we cannot guarantee a restroom at the very start of the tour, but we will have bathroom breaks along the route.

All of our regularly scheduled tours are given in English, but thankfully our humor is universal. We do offer private group tours in a variety of languages (French, Spanish, German, Dutch, Italian, Portuguese, Russian, and more). Just call ahead and we’ll make it happen.

First choice would be to walk to us. Chicago is flat and easy on the feet. Second choice for downtown tours would be taking a cab. Our shop and the Chicago Cultural Center are each a $5 cab ride from most downtown hotels. Third choice would be the local transit system’s trains and buses. If driving, here is the information below:

Bike Tours:
540 N. Lake Shore Drive. The entrance is on the south side of Ohio Street just west of Lake Shore Drive, just past the dry cleaner’s location. Please enter through the covered Driveway and once you’re through, turn right and follow the signs.
Parking: Please park at 441 E. Erie St., which offers the lowest rate in the neighborhood. Before leaving Bobby’s, ask us for a discount slip that reduces the rate to $14 for 6 hours. On Saturday and Sunday, you can park for up to 6 hours for only $12 and up to 12 hours for $16.

Walking Tours:
All of our walking tours begin at various locations around the City.  We encourage you to use Google Maps or Apple’s Siri to find directions and parking/public transportation suggestions.

Bobby’s sought long and hard to find the perfect designers and suppliers for our fashionable and oh-so-comfy t-shirts, tech-shirts, and stylin hats. You can purchase them online via our “Shop/Service” page or in our shop. We’ll even knock 10% off if you buy it on the day of your tour or rental.

We’re glad you want to join one of the friendliest organizations in the world. We are always looking for tour leaders with a positive attitude, strong leadership qualities, and a passion for Chicago history; previous guiding experience is a plus as well. We are also looking for Front of House leaders who are looking to get more from their summer work experience. We strive to offer our employees more than just a ‘job’, but a positive leadership program that will make you a successful person in life. Email employment@ bobbysbikehike.com and include your resume, cover letter, and a picture so that we can see your smiling face.

At Bobby’s Bike Hike Chicago, we take great pride in being the best. We have been the top rated tour company in Chicago since such rating services such as TripAdvisor have been around. Why? Our tour guides make all the difference in the world. We take our time during the hiring process, making sure to bring on only the best guides. And then we put them through an industry leading training program to make sure they are the best guides they can be. This process ensures that our guests have the best possible experience they can possibly have. And we take great pride in that process. Our Culture is another thing that stands apart from most. You can feel our culture right when you enter our shop or join one of our tours. We all believe in four tenets of Travel, Community, Health & Service. How that breaks down is we think of ourselves as Ambassadors of your Chicago Travel, we look to build a better local Community, we promote both our health and the health of our planet, and we believe in offering the best customer service possible.

All of our bikes have pouches on the front which can hold sweaters, purses, phones, water, etc. If you have larger things, we can store them at the shop while you are out on your tour or rental.  Families, feel free to leave your strollers with us.  Unfortunately, our walking tours do not leave from our shop and so we have no storage capacity.  Be sure to leave the extra packages, etc., at home or in the hotel before a walking tour.

 

General Chicago Questions

You’re going to learn a lot on our tours, but you can also receive City of Chicago information by going to the Chicago Visitor’s Center, located at the Cultural Center on Michigan Avenue and Randolph Street, where some of our walking tours begin.

YES! Chicago has consistently ranked as one of the top Cities in the country for biking and walking. It’s flat, attractions and neighborhoods are very close in proximity, and Chicago has extensive network of bike lanes, paths, and sidewalks to enjoy. Chicago boasts a 20 mile Lakefront Bike Trail, as well, that hugs Lake Michigan and connects all the major attractions to parks, beaches and Chicago’s top neighborhoods.

Oprah has moved out of Chicago, but her presence in Chicago is still felt to this day. Her old Streeterville penthouse is on our Lakefront Neighborhoods Tour route.
Barrack Obama has a house on the Southside of Chicago in Hyde Park. None of our tours get down there, but we provide bike renters a wonderful map to find his house and the Lakefront Trail takes you right to his beautiful neighborhood.

Chicago is called the City of Neighborhoods as it boasts a wide variety of distinct and diverse cultures represented from around the globe. While we could easily write a book a mile long on how many wonderful neighborhoods there are, we wanted to just list a few of our favorites here.
The Loop – Chicago’s business district and home to the highest concentration of Chicago attractions including the Chicago Riverwalk, Willis Tower, Millennium Park, State Street, Daley Plaza, and the Chicago Theatre.
Gold Coast / Streeterville – Chicago’s premier neighborhoods bordering the Lakefront, home to the most expensive properties in the entire City. This is where you’ll find the original Playboy Mansion, Oprah’s old Chicago condo, and countless other Chicago celebrities. It’s also where you’ll find the iconic Rush Street entertainment district.
Old Town / Lincoln Park – The quiet streets of Old town will have you believing you are a world away from the City, even though you’re right in the heart. The entire neighborhood is on the national historic register and streets are designed so that there is very little automobile through traffic. Many of our tours go through Old Town because it’s so nice to ride through. Lincoln Park is another upscale neighborhood with amazing boutique shopping along Armitage and adjacent park and zoo with same name.
Wrigleyville / Lakeview – Home to the Chicago Cubs. You can litteraly ride your bike to Wrigley Field as the Lakefront Trail connects downtown to the stadium, which sits just a couple blocks from the path. Wrigleyville is home to a number of bars and can be quite energized on game day. The surrounding neighborhood is Lakeview, home to a wide variety of eclectic enclaves including Boystown.
Andersonville is on the far north side and is Chicago’s original Swedish neighborhood. You can still see many of the original Swedish restaurants and shops today.
Wicker Park / Bucktown – Hipster central with great local shopping as well as trendy world-class boutiques. The epicenter of this cool neighborhood is North Avenue and Milwaukee Avenue. Worth a trip for sure.
Fulton Market / Greektown – Food, Food & more food define this area west of downtown that has quickly turned from Chicago’s old warehouse district into one of the hottest places to live and eat. Now home to Google and McDonalds Corporate Headquarters, this area is seeing some of the fastest growth among Chicago neighborhoods.
Pilsen – Chicago’s Mexican neighborhood where you can get some wonderful food, authentic flavor, and see beautiful art and architecture.
Chinatown – Chicago’s original Chinese community where you can witness all of the regions of China on full display with amazing food, colorful local shops, and an amazing street scene. Cermak and Wentworth is the epicenter of Chinatown.
Ukrainian Village – One of Chicago’s fastest growing real estate markets that mixes young Chicago families with old school Ukrainian and Eastern European traditions.
Bridgeport is home to Chicago’s hard working Irish and Italian families that have been the lifeline of Chicago politics and have helped build Chicago since the beginning. If you want to learn about old school Chicago, Bridgeport is your neighborhood. It’s also home to the Chicago White Sox.
Bronzeville is a beautiful African American neighborhood just south of downtown that has an amazing art and culture scene.
Hyde Park / Kenwood is Chicago’s established neighborhoods on the far Southside of the City and home to the University of Chicago and many old historic mansions, including Barrack Obama’s home.

Most of Chicago’s top attractions can be found along the Lakefront and in the downtown section of the City. A good rule of thumb to know is that the Chicago River runs east west right through the heart of downtown. So if you’re anywhere around the Chicago River, then you’re right in the heart of Chicago with easy access to most Chicago attractions. Those attractions include Millennium Park, Navy Pier, John Hancock Center, Historic Water Tower, Chicago Theatre district, Wrigley Building, Chicago Riverwalk, Cloud Gate, Crown Fountain, Chicago’s Lakefront, Grant Park, Buckingham Fountain, Daley Plaza, State Street, Oak Street Beach, Michigan Avenue. A little further north from downtown is Lincoln Park, the zoo, and North Avenue Beach, and Wrigley Field. A little further south of downtown is Museum Campus, Soldier Field, the Willis Tower, Union Station, and McCormick Place.

American Football – Chicago Bears play at Soldier Field
American Baseball – Chicago Cubs play at Wrigley Field (north side) / Chicago White Sox at Guaranteed Rate Field (south side)
Basketball – Chicago Bulls play at the United Center
Soccer – Chicago Fire play at Toyota Park Stadium
Hockey – Chicago Blackhawks play at the United Center

The local train system is called the ‘L’ because most of it is elevated above street level. It is operated by the CTA (Chicago Transit Authority), which also operates the buses and maintains a universal fare system for easy transfers. The “Directions” feature on Google Maps has full support for public transit options in Chicago and is an ideal way to plan your route.
Paying: If you take the ‘L’, you must prepay by going to a station and going to the self-guided kiosk. A one way ticket costs roughly $2.25, and you can make two transfers for $0.25 each within two hours of paying a one-way fare. The bus costs the same as the ‘L’ and allows you to just hop on and pay cash, but cash riders have no access to transfers. The bus drivers won’t have change but they’re usually very helpful if you tell him that you need help getting to your location.
Metra is the fast rail line that takes you between the City and the rest of Chicagoland. The costs vary depending on how far you are going. It’s less expensive to buy your ticket at the station, but you can just hop on and someone will come around and charge you the fee. The Metra reminds us of a cattle truck but it is a fun way to get to and from anywhere outside the city. We recommend sitting on the second story for the best views.

Yes, absolutely. While we do have our issues with crime, the highest rates of crime are limited to just a few distinct neighborhoods far from the downtown visitor district. So while you might read about crime in Chicago, it’s not something you will or should ever come in contact with if you are staying in downtown or one of the connecting neighborhoods.

The 20 mile Lakefront Bike Trail is one of the best bike trails in the world. It’s 100% car-free and allows you to experience life as a local, while riding up to Chicago’s top attractions. The trail connects downtown to the adjacent neighborhoods, parks, and beaches giving you ample opportunity to explore. You can also bike into Chicago’s unique and diverse neighborhoods, including the 606 Bloomingdale Trail through Bucktown, Wicker Park, and Humboldt Park.

January, February
Weather: Coldest Months in Chicago. Temps can range from 10-40 degrees Fahrenheit

What to Wear: Dress in layers because stores and restaurants will likely keep things warm. Bring a warm coat, scarf, hat, gloves, and some good weather resistant shoes.

March, April
Weather: March is not as frigid as February, but you’ll still need a warm coat. March temps can range from 30-50 degrees Fahrenheit.
What to Wear: Layers.  Bring a weather resistant, warm coat and maybe gloves. It probably won’t snow, but it has been known to snow in April.

May, June
Weather: Spring usually means warmer temps and more sun, between 50-80 degree.
What to Wear:  Layers.  May and June can shift wildly in temps, depending on which way the wind is blowing.  In May, a light spring jacket is probably the heaviest thing you’ll need.

July, August
Weather: Summers in Chicago are the BEST!  Hot, but usually not too hot. On really hot days, the lake usually does a good job of keeping us mild.  Temps range from 70-95.
What to Wear: Wear light clothing: natural fibers are best, especially cotton and linen.  But you might need a sweater at night.

September, October
Weather: Fall in Chicago is quite nice as well.   September gets a lot of sun, just not as hot as the summer.  Temps range from 65 to 85 degrees.  October gets a little cooler, especially at night.  Temps in October range from 55 to 80 degrees.

What to Wear: Layers!  Notice a trend?  Days and nights can vary drastically, warming up during the days and getting cooled off at night.  In September you can still wear summer clothes but bring along a jacket.  October cools off around here, so you’ll usually need a jacket.

November, December
Weather: Expect highs in the 40-50 range in November and 30-40 range in December.
What to Wear: Bring a heavier jacket and consider a hat, scarf, and gloves.

 

 

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