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Who is Bobby?
How long/strenuous is the tour anyway?
I couldn’t fit my bike in my suitcase. Do you have one I can use?
All the tours look like fun! Which one should I take?
How large are the groups? What can I expect?
What is your cancellation policy?
Should I purchase tickets in Advance?
I’m bringing an infant/very young child. Should I purchase them a ticket?
Can I leave my things at your shop during the tour/rental?
I took this tour a year ago. Has anything changed?
Are tours only offered in English?
Do you offer discounts for travel agents?
Can I book a private tour?
Should I tip the guide on the bike tour?
Can we rent bikes seperately from the tour?  What about overnight rentals?
Where are you located? How do I get there and where can I park?
How should we get to you? How do we use/pay for the transit system?
Where does Oprah live? Where does Barack Obama live?
Where is Tourist Information?
Are gift certificates available?
How do I get a T-Shirt?
How do I become a tour guide?  What other positions are there?
Who is Bobby?

Bobby's Bike Hike was founded in 2002 by Jeremy Lewno, 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!



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How long/strenuous is the tour anyway?

strenuous, adj: requiring or using great exertion. Thus began my high school graduation speech, and, although it described getting into college, it is not applicable to Bobby’s Bike Hike.  Both of Bobby's 'Lakefront Neighborhoods' and 'City Lights at Night' Tours are set at a relaxed pace, covering about 6-8 miles in 3 hours, including a small break at a quiet, outdoor café'/beer garden just in case you need a snack. By the way, snacks are ala carte and not included in tour price. If you are a group leader, and would like to include breakfast/lunch/dinner into the price of the tour, just let us know and we’ll make it happen.  If you're looking for a little bit more riding, you might check out our brand-new, and ridiculously impressive, 'Bike Obama Chicago' Tour which covers 20 miles in 4 hours, taking you to the unique and beautiful Hyde Park neighborhood.

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I couldn’t fit my bike in my suitcase. Do you have one I can use?

No bike, no problem! We have hot deluxe cruisers for you to ride, and helmets to keep you safe. Each bike is labeled with a name that describes its personality, but you can also tell them apart by their distinctive markings and behavior. They each have baskets for your convenience. Although we recommend riding our bikes, you can bring your own and save $5. All Bikes are Deluxe Cruisers with fat tires, cushy seats, and fenders to keep you clean.

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All the tours look like fun! Which one should I take?

Each tour is unique and ideal for all ages and fitness levels.  Of course, we suggest taking them all. Bobby’s ‘Lakefront Neighborhoods’ tour is our signature tour, taking you off the beaten path and into Chicago’s most popular neighborhoods, parks, and beaches, giving you a glimpse into ‘real’ Chicago life.  Bobby’s ‘City Lights at Night’ tour has been extremely popular as well, providing a healthy and fun alternative to Chicago nightlife and the skyline fireworks.  Bobby’s brand new‘Bike Obama Chicago' Tour is a longer ride than the others, orientating you to Chicago’s unique and beautiful Hyde Park neighborhood, the site of our President's former university and current Chicago home.  You can combine any two tours and save 10% off your ticket price. Easily reserve online or call ahead (312-915-0995) to reserve both spots.

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How large are the groups? What can I expect?

Expect to explore Chicago with 20-25 of your closest friends, learn about its history and have unparalleled fun. Gosh, we set the bar so high, it’s a wonder people don’t go home disappointed, but they don’t! Amazing! Chicago was recently voted the "best bicycling city in North America" by Bicycling Magazine. You'll see why when you cover more ground than a walking tour while avoiding the constant diesel rumble of a bus tour.

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What is your cancellation policy?

Why would you want to cancel? If there is an unforeseen change in your schedule, don’t worry, you can cancel your tour with 72 hour notice. Tours are offered from March through November because these are the months you can usually rely on good Chicago weather. Tours do run rain or shine. If there’s one thing we’ve learned, it’s that weather forecasts are often unreliable. Chicagoland is huge, so if they predict a shower, it probably won’t affect the tour. If a brief shower does occur, we'll provide raingear for the group. In the rare event that a tour is cancelled due to weather, we will allow you to reschedule your tour, subject to availability.  You should dress appropriately for the day's weather conditions.

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Should I purchase tickets in Advance?

YES!  We’re popular and not afraid to admit it. We suggest buying tickets in advance for a number of reasons. This will not only guarantee your spot on the tour and save you money, but will save time once you arrive at the tour. By paying online, we’ll immediately email your E-ticket, which you’ll print and show to your guide, and off you’ll go for three hours of Chicago fun. Plus, you’ll save 10% off of our walk-up prices.

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I’m bringing an infant/very young child. Should I purchase them a ticket?

Don’t worry, children 3 and under will not be charged a full kid price. Your small child will, however, be charged a $5 ticket price which goes toward reserving their special equipment. Please let us know how many infants/young children will be attending and mark any needed special equipment (child seats, trailers, tag-a-longs) when you purchase your tickets.

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Can I leave my things at your shop during the tour/rental?

All of our bikes have pouches on the front (We call them bike fanny-packs) 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

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I took this tour a year ago. Has anything changed?

Yes. We change the tour slightly each year. Many parts of the tour remain the same, but we do our best to improve upon and enhance the tour each and every time we go out.

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Are tours only offered in English?

No. Please note that while all of our regularly scheduled tours are given in English, our humor is universal. We do, however, 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.

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Do you offer discounts for travel agents?

The travel agent discount is our standard 10% off Adult Ticket. Please reserve online to receive this discount, or supply a business card at the time of tour.  

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Can I book a private tour?

Yes, private tours are available for groups of up to 250 people. To inquire about a private tour, please Click Here. Bobby’s Bike Hike will contact you immediately to inform you if the date and time requested is available.

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Should I tip the guide on the bike tour?

We've found there to be a number of answers to this question. We think that a tip is a direct reflection on how you thought the tour guide performed. 10% to 20% suggested gratuity if you had a good time. More if you had a GREAT time. The guide will be happy to take the extra cash.

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Can we rent bikes seperately from the tour?  What about overnight rentals?

Yes, you can rent and go on your own.  While Bobby's prides itself on being a tour operator first and foremost, we realize that some people prefer to ride on their own.  Our location is perfectly situated downtown right on the 18-mile lakefront path.  Our convenient location between Michigan Avenue and Navy Pier (on Illinois Street and McClurg) make it easily accessible from all downtown hotels.  During the peak summer months from Memorial Day to Labor Day, we open up a second location in Lincoln Park at Diversey Harbor.  That location has rentals only (no tours) and not available for repairs of any kind.  With your rental, Bobby's provide you a bike, helmet, lock, and map so you know where you are going.  You may rent by the half day, full day, or overnight and weekly.  Just visit our website rentals page and reserve ahead, saving 10%.

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Where are you located? How do I get there and where can I park?

Hey, that’s three questions. 465 N. McClurg Court. The entrance to the pedestrian walkway leading to us is located on the southeast corner of Illinois Street and McClurg Court, located at the southeast corner of Illinois Street & McClurg Court intersection. Just follow the walkway down to the end and you’ll see us. Parking in downtown Chicago can be tricky, even if you are a Chicago native—especially if you are a native (see: city stickers, street cleaning, and permit parking). So, try to leave your car at home. If you must drive, please park at 322 E. Illinois Street where we've arranged a discounted rate of $16 for 5 hours.  You must validate your ticket with us at the Bobby's Bike Hike shop.  Please visit our LOCATIONS page for a detailed map to parking, as well as important parking directions on how to validate.  If no car, please consider a cab or take the metra or public transport (see question #17) into the city. Six CTA buses go directly to River East Plaza: the 29, 56, 65, 66, 120 (express bus from the Northwestern Train Station) and the 121 (express bus from Union Station). Call the CTA at (312) 836-7000 for specific directions from your location, or visit www.transitchicago.com and www.metrarail.com. Make sure you step off at McClurg Ct stop. Better yet, Click Here to view our location map with driving directions and our discounted parking suggestion.

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How should we get to you? How do we use/pay for the transit system?

First choice would be to walk.  Chicago is flat and easy to walk.  Second choice would be taking a cab.  We are a $5 cab ride from most downtown hotels.  Third choice would be the local transit system.

If you drive, please park at 322 E. Illinois Street where we've negotiated a discounted rate of $16 for 5 hours.  You must have your ticket validated at our shop.

The local train system is called the 'L' for its elevated positions throughout the city. It is operated by the CTA (Chicago Transit Authority).  IF you have access to the internet then you can go to www.transitchicago.com and click on trip planner. Trip planner will tell you the quickest way from your location to where you want to go. It will also show you by which method and how much money.

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 $2.00. The bus costs the same as the 'L' but you just hop on and pay. The bus drivers won't have change but they will be your best friend if you tell him that you need help getting to your location. Be nice and they should help you out.

If you have to get out of the city, then you may want to look into taking the metra, which is the fast rail line that takes you out to the rest of Chicagoland. The costs vary depending on how far you are going. Just hop on and someone will come around and charge you the fee. You do not have to prepay on certain trains.  Please ask information or the ticket booth if you are unsure. The metra reminds me of a cattle truck but it is a fun way to get anywhere outside the city. I recommend sitting on the second story for the best views.



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Where does Oprah live? Where does Barack Obama live?


Oprah actually has a couple of places she owns around Chicago. When you're the richest woman alive you can afford such luxuries. Bobby’s ‘Lakefront Neighborhoods’ tour actually makes a stop right in front of her main house. She is a huge fan of the tour and she might even wave to us.

Obama lives in Washington DC right now.  But when he returns to Chicago, he stays in his house in the beautiful neighborhood of Hyde Park.  There is so much to see around his house and neighborhood, including the University of Chicago.  Try taking Bobby's brand-new 'Bike Obama Chicago' Bicycle Tour.  It's a great way to see the President's Chicago neighborhood.


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Where is Tourist Information?

You can receive City of Chicago information by going to the Chicago Visitor's Center, located in the pumping station, across the street from the Historic Water Tower. The exact address is 163 E Pearson Street (Southeast corner of Michigan Ave and Pearson Street).  You can also try the Cultural Center on Michigan Avenue and Randolph Street.


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Are gift certificates available?

Yes, gift certificates are available for all of our tours. To purchase a gift certificate, please Contact Us.

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How do I get a T-Shirt?

These T Shirts cost Bobby more to produce but are well worth it. They are soooo comfy and fit nice in the arms. $15 for short sleeve, $20 for long sleeve.  $40 for a sweet hoodie.  Just Contact Us.

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How do I become a tour guide?  What other positions are there?


Join one of the friendliest organizations in the world.  We are looking for tour leaders with a positive attitude, strong leadership qualities, a passion for Chicago history, and previous guiding experience.  We are also looking for Rental Service leaders who are looking to get more from their summer work experience.  We strive to offer our employees more then just a 'job', but a positive leadership program that will make you a successful person in life.  Contact Us to send in your resume, experience, along with a picture so that we can see your smiling face. Our season is from March to November.

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