Cake icon

We’re celebrating 10 years of Wanderu by giving away $10,000 in free travel!  See details ››

Chicago Travel Guide: Exploring the Windy City

Chicago is a fantastic city to live in and to visit, especially if you are fond of waterside restaurants and beer gardens, skyscrapers, fancy boats rides, and delicious meals. Knowing that the famous Windy City is large and could be overwhelming for first-time visitors, we have come up with a complete guide of go-to attractions that every traveler who arrives in Chicago must check out, even if the stay is rather brief.

We have included interesting activities, iconic city locations and some memorable eateries and hotels. Read on and plan your outing to the coolest city in the Midwest!

Things to Do in Chicago

Soldier Field is conveniently located in the South Loop right near the heart of downtown Chicago, so you’ll find plenty to do nearby.

Eat great food

If you came to Chicago and didn’t have pizza, shame on you! Pizza is a must and one of the best options to get a slice is Flo & Santos, well-known pizza and pierogi restaurant located near Chicago’s South Side around Soldier Field Stadium. Flo & Santos becomes a bit more “social” after 8 p.m., when its outdoor beer garden comes alive.

If the pub scene isn’t appealing to you, you could try Eleven City Diner. This casual restaurant is also located in the South Loop at 1112 S Wabash Ave. It is a family-owned diner that serves breakfast all day, as well as your classic soups, salads and sandwiches.

Stop by the Must-See Attractions

If this is your first time in Chicago, you should consider doing some touristy things that are, in the end, super worth it. One Instagram-worthy place you can’t miss is the Cloud Gate sculpture, otherwise known as “The Bean.” This 110-ton elliptical sculpture sits in the center of AT&T Plaza at Millennium Park in the Loop area of Chicago. The stainless steel bean reflects Chicago’s famous skyline and the clouds above, creating a must-see view for everyone.

Another place worth visiting is the Buckingham Memorial Fountain, one of the largest fountains in the world. Bonus: Millennium Park and the Buckingham Memorial Fountain are both excellent places in Chicago to write.

Check out Navy Pier

Odds are you’ll be walking the city or taking public transportation while you explore Chicago, so at some point you’ll need to make a pit stop for some food and a cold beer. The perfect place to refresh and refuel is Navy Pier’s Miller Lite Beer Garden, which is one of Chicago’s most popular outdoor venues to enjoy food, drinks and live music.

This beer garden has fantastic views of the magnificent skyline in Chicago and one benefit is that there’s never a cover charge! It’s a perfect pit stop before making your way around the rest of the pier.

After you check the Beer Garden off your list of must-experience things to do, go ahead and make your way to Navy Pier’s iconic Ferris Wheel. Although it may seem a bit frightening that it is 150 feet tall, once you get to the top, the view will be well worth it.

While on the pier, make sure to visit Jimmy Buffet’s Margaritaville. With the extensive choice of fresh-made cocktails and an abundance of food selections from the menu, you’ll be humming the tunes of Jimmy Buffet in no time.

Although it may not be such a great decision to do something exhilarating after your cheeseburger in paradise and an ice cold beer (or two) from the beer garden, you might decide that you’re up for something adrenaline-pumping. If that’s the case, there’s a Navy Pier Seadog Boat Cruise that leaves right from the pier.

The Seadog Boat Cruise offers a 30-minute speedboat ride on Lake Michigan that takes you around twists and turns 30 percent faster than any other boat ride in Chicago. Once your boat ride comes to an end, stop by the Crystal Gardens for a lovely photo op set among full-size palm trees, fountains, exotic flowers and wildlife.

Make Your Seg-Way Around the City

Instead of walking throughout the entire city of Chicago, you could glide along the streets on a Segway! Riding a Segway is one of the best ways to see the city and all of its memorable landmarks.

Steve’s Segway Tours is one of the highest-rated tours in the city of Chicago. Glide around with Steve himself as he leads a variety of tours throughout the city. You can choose between the Lakefront/Museum Campus Tour, the Architecture Tour, the Fireworks Tour, the Haunted Chicago Tour, and a handful of other options.

Celebrate with some drinks

You’re in Chicago, enjoying a memorable getaway, so there is plenty to celebrate. In the city there are plenty of bars to choose from that serve a variety of craft beers and a selection of pub food.

Another very cool option, especially if you love boats, is Weathermark Tavern. This nautical-themed bar captures the spirit of Chicago’s lake fleet. Sails hang from the ceiling to the floor creating semi-private casual areas with couches and cocktail tables.

Don’t miss this tavern’s famous happy hour, Monday-Friday from 3 p.m. to 6 p.m. You can enjoy $2.00 off all drafts or something else from their menu at a great price.

Where to Stay in Chicago

The Best Western at Grant Park has one of the best value rates among all of the hotels in the city. The Best Western is in the South Side of Chicago and is averaging around $170 per night. Aside from the “make yourself at home” atmosphere that this Best Western provides, the outdoor pool and on-site restaurant are a huge plus.

Click here to find the best deals on hotels and hostels in Chicago.

For more ideas on fun things to do around Chicago, check out this article by the Travelling Salesman.

Book a cheap ticket to Chicago on or by downloading the Wanderu app and enjoy outing to the Windy City!

About Lindsay Tavarozzi: Lindsay is an aspiring travel journalist who loves caramel iced lattes, passport stamps and her Nikon D5200. She spends her free time writing posts for her blog and binge-watching Gossip Girl. Lindsay is a graduate from Lasell College with a Bachelors in Communication.

Like what you read?
Spread the word:

About the author
Karina Barriga Albring

Karina Barriga Albring

I'm a writer, journalist, soccer lover and hot sauce enthusiast born and bred in the mighty Andes. Wanderlust hit me hard at a young age and since then, it keeps me up at night. NYC and Modena, Italy changed my life, but my favorite destination is still Rio de Janeiro – and not only for the 'futebol'!

Wander with us!

No monkey business, just cheap deals on bus & train travel, straight to your email inbox

Come wander with us!

Follow us for travel hacks, inspo, and deals right in your feed: