Chicago can be an overwhelming city to visit for the first, second, fifth, and tenth times. Okay, even us local-Chicagoans are overwhelmed from time to time. That’s not so bad though – it just means you have a lot to look forward to on your trip! So grab your pen or pencil, a piece of paper, and the deepest piece of pizza you can find, cause you’ll wanna take notes as you read through this article! If you’re looking for a bike rental to cruise around town on or you’re in the market for a local tour guide to give you the lowdown – give Bobby’s Bike Hike a shout and let us help you out!

5 Must Do Activities in Chicago

Tour Chicago with Bobby’s Bike Hike on Bike, Food and Walking Tours

This wouldn’t be one of the best Chicago guides if we didn’t send you to the very best things to do in Chicago. Whether by bike or by foot, the expert guides at Bobby’s Bike Hike will deliver quality information, group interaction, and most importantly, fun. Oh, did we not mention the food? Many of Bobby’s tours sample Chicago foods such as deep dish pizza, hot dogs, and craft beer. While the beer tours are catered to the adults (the 21st amendment sadly strikes again), they have a Tike Hike which is great for families. Group sizes range from 4 to 18 per guide and private tours are available. Spring, summer and fall are definitely the best times to check out Bobby’s bike tours, but the food and walking tours run all year round.

bobbys bike hike chicago bike tours


Hit up a Chicago Street Festival

All year long (but especially in the summer months because #PolarVortex), Chicago hosts hundreds of street festivals in and around its 200+ neighborhoods.  One of the best things to do in Chicago is to look up “Chicago events near me” and discover which festivals are going on. They can get pretty specific, like Pilsen’s “Mole de Mayo”, a celebration dedicated to sauce! Some of our personal favorites are the Windy City Smokeout, Pride Parade, Chicago Gourmet, World’s Largest Block Party, and Do Division.

two chefs at Chicago Gourmet serving food

*Photo of Chicago Gourmet, courtesy of

Visit an Improv Show

Sketch comedy and improv shows are top on the list of fun things to do in Chicago. If you love Saturday Night Live, visit Second City where many of the famous folks who graced the SNL stage originated, including Tina Fey (she’s a pusher, she pushes people), Tommy Boy Chris Farley, and OG Blues Brother Dan Aykroyd. Another great option is iO (Improv Olympic) where competing improv teams battle each other in friendly and funny competitions. Their new location in Lincoln Park boasts four theatres, an expanded Training Center, two bars, a beer garden, and a kitchen.

Second City Comedy Bachelor Party Ideas

*Photo of Second City’s ‘Dream Freaks Fall From Space’ by Todd Rosenberg, courtesy of

Concert at Northerly Island

Do you like live music? Northerly Island (in the summer) is one of the best places to see concerts in Chicago. Northerly Island sits on Lake Michigan, on what used to be an old runway. The airport is long gone, thanks to a former mayor secretly bulldozing it in the middle of the night, but in its place is a great park and a fantastic summer concert series. At Northerly Island, you can listen to your favorite band with Chicago’s gorgeous skyline as the backdrop. But is it better than listening on vinyl??

Multi-colored lights at Northerly Island concert venue

*Photo courtesy of

The Ledge at Willis Tower

Other options for fun activities in Chicago include visiting the Ledge at the Sears Willis Tower. Once the tallest building in the world (back when it was the Sears Tower, oh how the mighty have fallen), you can stand 1,353 feet above the ground in an all glass box and tower over the city. But if you’re scared of heights, you might want to sit this one out.

looking down at Chicago from the willis tower skydeck

*Photo courtesy of

5 Must See Attractions in Chicago


Chicago Mile Lakefront Trail

Chicago’s lakefront parks form our front yard along the crystal clear blue waters of Lake Michigan. The lakefront’s 20 mile bike trail stretches from the north to the south and is a picturesque way to view the City. Check out Bobby’s Bike Hike for a bike rental, helmet, and trail map, then set off on your adventure! You can visit the Lincoln Park Zoo (for free!), many beaches including North Avenue Beach (Chicago’s most popular…and rowdiest), as well as Grant Park and Lincoln Park. Park your bike at Museum Campus and take a break in a museum or visit Soldier Field, where the Chicago Bears play {American} football. If you’re more of an America’s-favorite-pastime fan, head over to Wrigley Field to watch the Cubs play!

Bicycle riders in Chicago's lakefront neighborhoods area | Bike Tours Chicago

*Photo courtesy of Bobby’s Bike Hike

Millennium Park

A bean. A clamshell. The fountains of 1000 faces. Discover state-of-the-art architecture, landscape design, and sculptures that provide the backdrop for hundreds of free cultural programs including concerts, exhibitions, tours, and family activities. Millennium Park is a can’t miss Chicago attraction and home to the Jay Pritzker Pavilion, designed by world renowned architect Frank Gehry. The park famously houses the shiny sculpture Cloud Gate (AKA ‘The Bean’ AKA a-drop-of-liquid-mercury-before-it-touches-the-ground AKA ‘The Bean’), designed by British artist Anish Kapoor and Crown Fountain, the fountain of a 1000 faces designed by Spanish artist Jaume Plensa. Some of the best Chicago events occur in the Park, including a summer film/concert series and various food tastings.

Millennium Park Chicago outdoor film screening

*Photo courtesy of

Buckingham Fountain at Night

Many people visit Buckingham Fountain during their stay in Chicago, but not enough visit at night during the music and lights show, a spectacle that puts Busby Berkeley to shame. Dedicated in 1927, it is one of the largest fountains in the world. Resembling a rococo wedding cake, it was inspired by the Latona Fountain at the Palace of Versailles. Buckingham Fountain operates from April to October, and if you attend, we recommend you stand at the southeast corner for the best pictures of the skyline and fountain together. There are a few tour groups who make stops at the fountain for night viewings, one of them being the Electric Bikes @ Night Tour.

Chicago buckingham fountain at night

*Photo courtesy of

Visit Some Chicago Neighborhoods

Chicago is a city of neighborhoods, with many distinct and unique areas of town to choose from. The Gold Coast neighborhood on the near north side houses old, opulent mansions that makes it home to many a Chicago celebrity (as well as architectural celebrity the Playboy Mansion). Old Town is the former artists’ village turned historic district with its quiet core in the heart of the City.  Wrigleyville provides a rambunctious and lively bar scene, especially when the Cubs (baseball) play in Chicago. Bucktown/Wicker Park is Chicago’s funky, hipster neighborhood where you’ll find unique shopping and an eclectic restaurant scene. Pilsen has an amazing art scene as well as the tastiest Mexican food. But if you’re looking for the best Chicago restaurants all within the same neighborhood, the blossoming West Loop and Fulton Market are the places to be with the products of famous restauranteurs including Rick Bayless, Sarah Grueneberg, and the Boka Restaurant Group. To check out some neighborhoods by bike, here are two tours we recommend for your trip: Westside Foodie Ride and the Lakefront Neighborhoods Bike Tour.


Garfield Park Conservatory

Chicago has beautiful architecture and an awe-inspiring skyline, but sometimes you need to escape the man-made and return to nature. The Garfield Park Conservatory houses an outstanding collection of plants and flowers and hosts fun, (relaxing?) events like goat yoga. Touch a tree whose leaves are bigger than you, or read a book by the begonias. The Conservatory is free to visit year round, just like nature should be.

bright green trees and plants at the garfield park conservatory

*Photo courtesy of

5 Can’t Miss Events in Chicago


Join 25k People Riding Bikes on LSD

Not to confuse the drug with the Drive, we’re talking about closing down one of Chicago’s most iconic stretch of roads, Lake Shore Drive (LSD), to make it bike-friendly and car-free. This takes place the Sunday of Memorial Weekend on the last weekend of May. Bike down Lake Michigan with the sun rising on the east and the breathtaking skyline to the west. This event benefits the Active Transportation Alliance, which advocates for better bike, walking, and transit in Chicago. If you need a bike for the event, look no further than this bike rental space in downtown Chicago!

Chicago sightseeing tour of cyclists riding Lake Shore Drive | Bobby's Bike Hike


Chicago Blues Festival

Chicago’s history with blues music is legendary. Urban blues evolved from classic blues following the Great Migration of African Americans from the southern United States to the industrial cities of the north. Southern migrants brought the blues to Chicago, where the music helped them forge connections and transform an unfamiliar, often inhospitable city into a new home. The music was also transformed—electrified and amplified – to compete with urban noise. Chicago’s Blues Festival is one of the best in the country, taking place the first weekend of June in Millennium Park.

guitar player in front of audience

*Photo courtesy of


Catch a Game at Historic Wrigley

Wrigley Field, which was built in 1914, is the second-oldest ballpark in the majors behind Boston’s Fenway Park (1912). Nothing beats a day at the ballpark where you can catch some sun, sing ‘take me out of the ballgame’, and enjoy a Chicago style hot dog. After the game, enjoy the surrounding neighborhoods of Lakeview and Boystown for a lively scene. Murphy’s Bleachers is one of our personal faves; they have a friendly staff and amazing beers on tap. The Chicago Cubs play during the spring, summer and early fall. And if these lovable losers are lucky enough, they’ll be playing into October as well!

outside wrigley field

*Photo courtesy of

Taste of Chicago Foodie Tour

Does the sound of almost 100 of Chicago’s top restaurants dishing out food in the same couple of blocks sound good to you? And what if we told you admission was free? Taste of Chicago is the world’s largest, free-admission outdoor food festival and is held annually in mid-July. The annual lakefront extravaganza lets you fill up on all the flavors of the city, from classic Chicago specialties to international cuisine. There is also live entertainment nightly from the Portillo band shell. So come on down and taste Chicago!

two women eating at Taste of Chicago

*Photo courtesy of


Chicago Lollapalooza

Lollapalooza is a four-day outdoor music festival in early August that hosts more than 100 alternative rock, punk rock, heavy metal, and hip hop bands as well as comedy, dance, and craft booths. Conceived and created in 1991 by “Jane’s Addiction” singer Perry Farrell as a farewell tour for his band, the event bounced around before it found a solid home here in Chicago’s Grant Park. They even offer kids-a-palooza if you want to bring your child to the event. Kids enjoy drum circles, face painting, and arts & crafts while listening to slightly kid-friendlier tunes.

looking over the crowd from the back of lollapalooza

*Photo courtesy of

5 Must Eat Foods in Chicago

Deep Dish Pizza

Chicago is a pizza town, that’s for certain. Sure, we didn’t invent it, but we created our own style and brand. The most popular Chicago innovation is the Deep Dish pizza. It is often reported that this oozing innovation was invented at Pizzeria Uno’s by founder Ike Sewell. However, a 1956 article from the Chicago Daily News asserts that Uno’s original pizza chef Rudy Malnati developed the recipe and should be credited with the creation. Piracy! Plagiarism! Infringement! Scandal aside, what makes this pizza unique is that the order in which ingredients are placed on a deep dish pizza is ‘backwards’ from a thin crust pizza. Deep dish pizza is made with slices of mozzarella cheese placed directly on the dough. Then additional ingredients like mushrooms, onions, and sausage are spread on top of the cheese. The pizza is covered with a fresh tomato sauce containing chunks of pear and plum tomatoes, then topped off with a sprinkling of cheese and spices. For the best Chicago pizza, we have two suggestions. Go old-school with the Deep Dish Malnati Classic at Lou Malnati’s restaurant. Splurge the extra buck to get the butter crust, and request that the sausage be in flat, patty form instead of crumbles. Option two is the deep dish pizza v2.0, the Famous Stuffed Chicago Classic Deep Dish from Giordano’s, which has a flakier crust and not one but TWO layers of bread.

deep dish chicago classic pizza slice being picked up

Chicago Hot Dog

There is no act more American than piling a bunch of delicious toppings onto a hot dog, and no place on earth takes this more seriously than the Windy City. People say that Chicago dogs are “dragged through the garden” because of all the toppings (sport peppers, pickle, mustard, sweet relish, onion, tomato, and celery salt). Maybe it’s true, but that garden never, ever, grows ketchup. Grab a dog at Max’s Take Out at 20 E Adams St and the Weiner Circle  at 2622 North Clark Street, an institution known equally for its dogs as its verbal jousting.

Chicago style hot dog

Italian Beef

Created on the South Side of Chicago in the Italian enclaves around the now defunct Stockyards, the classic Chicago Italian Beef Sandwich is a beautiful, drippy, messy variation on the French Dip. It’s. So Good. The Italian Beef is created by slowly roasting lean beef, slicing it thin, soaking it au jus, and layering it onto a crusty bread. The meat is typically topped with sautéed green or red peppers for a sweet flavor or giardiniera for a hotter flavor. Some of Chicagoland’s most popular spots to get Italian Beef are at Johnnie’s Beef at 7500 W North Ave, Elmwood Park and Bongiorno’s at 405 N. Wabash in downtown Chicago.

Portillos italian beef sandwich loaded up

*Photo courtesy of Top Secret Recipes

Cheese Curds

Some cheeses are born to be spread on bagels, others to be sliced and laid upon sandwiches. But cheese curds exist as an entity of their own because cheese doesn’t need an excuse. We must pay homage to our Midwestern brother Wisconsin, for they gave us the cheese curd, and nothing can repay our debt of gratitude. Its most distinctive feature is its squeakiness when you bite into a curd. If it doesn’t squeak against your teeth, I’m sorry, but you’ve been bamboozled. Will’s Northwoods Inn on 3030 N. Racine St take cheese curds to the next level by frying them in beer batter, and Mordecai’s Whiskey & Grill on 3632 N Clark Street kicks them up a notch with some spicy togarashi seasoning


Chicago Craft Beer

You might wonder why beer made the “Must Eat Food’ list. We don’t need to justify ourselves; once you’ve had some Chicago craft beer, you’ll be glad it was on here. You still want a reason? Ummmm, beer has barley which is used in cereal and salads and if those are foods then craft beer is too. Happy? You’ll be happier after a craft beer. Goose Island is one of Chicago’s most well-known craft brewing companies, with options like the Green Line (named after a section of the Chicago ‘L’) and the 312 (named after Chicago’s area code). They offer tours at their breweries (located at 1800 N Clybourn Ave and 1800 W Fulton St), which also include taprooms!

Goose Island beer taps

*Photo by Jose M Osorio



Well, we called this the Ultimate Tourist Guide, but we couldn’t include everything. For more travel information on Chicago, such as hotels, flights and car rentals check out this Chicago travel guide from KAYAK. What places and events would be in your Ultimate Tourist Guide? Comment below to make this page even more ultimate! Experience Chicago yourself and jump on a tour with us at Bobby’s Bike Hike!

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