Photograph by: Amanda

Best Things to Do in Chicago

Featured Chicago Travel Tips
  • Go on a sculpture walk and see The Bean at Millennium Park
  • Experience an authentic Chicago baseball game
  • Check out a local blues club or book in a comedy show
  • Get your steps in with the Chicago Riverwalk
  • Plan a tour of Chicago at sunrise to beat the crowds
  • Visit ​​North Avenue Beach & Lincoln Park at sunset for city views
  • Capture memories on a Flytographer photoshoot

Since 2013, Flytographer has captured millions of vacation photos all around the globe and know our customers have the best travel tips to share! Explore their favourite things to do in Chicago, best restaurants in Chicago, and general travel tips to get fresh inspiration and start planning your trip to Chicago.

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Jenna's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

Pizzeria Uno! The best deep dish pizza and a great atmosphere.

What are the best things to do in Chicago?

You have to do the architecture boat tour. An incredible way to see the city. And if you can catch a game at Wrigley Field do it! It's a magical place.

What is the best tip for a romantic getaway in Chicago?

Find a rooftop bar and enjoy happy hour. Enjoy wandering around the city. Walk around with no real destination.

Visited Chicago in July

Photo Shoot Location: North Avenue Beach

Amanda in Chicago for Flytographer

Sunrise's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

Andy's Jazz Club to see the Windy City Ramblers was an incredible experience.

What are the best things to do in Chicago?

Architectural boat tour with Wendella was the absolute best experience as a first-time tourist in Chicago. I learned so much about this great city on that tour.

Visited Chicago in June

Photo Shoot Location: North Avenue Beach

Maurice in Chicago for Flytographer

Rebecca's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

Three Dots and a Dash is such a cool speakeasy. They have the best group drinks and my Bachelorette's loved the dry ice and fire that embellished our drinks as they arrived. The Polynesian theme is so cool!

What are the best things to do in Chicago?

Whirlyball and Chicago Cycleboats were the two best activities in my opinion for a group our size (10 people). Everyone loved the party boat vibe and views on the Cycleboat and Whirlyball was easy to learn and a lot of fun. It's bumper cars meets lacrosse meets basketball.

What is the best tip for planning a bachelorette in Chicago?

Be sure to rent an Airbnb close to the downtown area so you can walk to places since the traffic can be bad. I rented a limo at night and everyone loved simply driving around in a limo blaring music. Also, we did a spray paint and sip class that we all loved and we had a souvenir canvas of our own design to bring home!

Visited Chicago in September

Photo Shoot Location: The Bean at Millennium Park

Maurice in Chicago for Flytographer

Jose's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

There's too many to list, but The Bento Box is definitely up there- it's a fusion of bar and restaurant- Japanese Speakeasy vibe

What are the best things to do in Chicago?

The Sumo + Sushi event was actually pretty great!

Hometown Shoot in July

Photo Shoot Location: Custom Route

Brandon in Chicago for Flytographer

Sadie's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

Lucky Dog! I grew up around Chicago, so I know Lucky Dog has the best hotdogs and beefs around!

What are the best things to do in Chicago?

The Color Factory, Drunk Shakespeare, and fireworks at Navy Pier.

What is the best tip for celebrating your birthday in Chicago?

Chicago has it all: Water celebrations, quiet spas, nature, landmarks, museums, adrenaline-rushing activities. Pick a couple of things to do and see where the wind takes you! Don’t forget to try the famous food dishes there!

Visited Chicago in June

Photo Shoot Location: Custom Route

Maurice in Chicago for Flytographer

Kristen's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

Galit

Visited Chicago in November

Photo Shoot Location: Chicago Riverwalk

Brandon in Chicago for Flytographer

Jenna's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

Pizzeria Uno! The best deep dish pizza and a great atmosphere.

What are the best things to do in Chicago?

You have to do the architecture boat tour. An incredible way to see the city. And if you can catch a game at Wrigley Field do it! It's a magical place.

What is the best tip for a romantic getaway in Chicago?

Find a rooftop bar and enjoy happy hour. Enjoy wandering around the city. Walk around with no real destination.

Visited Chicago in July

Photo Shoot Location: North Avenue Beach

Amanda in Chicago for Flytographer

Victoria's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

River Shannon in Lincoln Park because they allow dogs to come inside and run around

What are the best things to do in Chicago?

The architectural boat tours are our favorite, you learn all about Chicago's history and get stunning views you can only see from the river. Bonus points if you go at sunset!

Hometown Shoot in June

Photo Shoot Location: Lincoln Park

Amanda in Chicago for Flytographer

Cindy's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

I like Portillo's!

What are the best things to do in Chicago?

Art institute of Chicage, 360 Chicago, shopping at Magnificent Mile.

Visited Chicago in January

Photo Shoot Location: Lincoln Park

Brigette in Chicago for Flytographer

Ryan's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

Gibson's Italia, great food, great atmosphere, great drinks, wonderful service! 5 stars

What are the best things to do in Chicago?

Walking around downtown, the Navy Pier, Wrigley Field, the Art Institute, Willis Tower Skydeck, Soldier Field (Red Hot Chili Peppers concert)

Visited Chicago in August

Photo Shoot Location: Custom Route

Monica in Chicago for Flytographer

Jack's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

Pops Champagne Bar was the perfect first stop after our proposal!!

Visited Chicago in May

Photo Shoot Location: North Avenue Beach

Christian in Chicago for Flytographer

Robert's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

RAMEN-SAN in West Loop. Mara and I are both big ramen fans and their low-key setting with great food is always an excellent choice.

What are the best things to do in Chicago?

The zoo and surrounding area is for sure one of our favorite areas in the city. It's popular for a reason :)

Visited Chicago in January

Photo Shoot Location: Lincoln Park

Lukas in Chicago for Flytographer

Rini's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

For breakfast grab and go is La Colombe Coffee Roaster, Dinner at SKY and Lunch at Joy Yee in Chinatown, they have the best Boba Tea!

What are the best things to do in Chicago?

We had appointments for photoshoot and we visited Art museum of Chicago, Millennium park and Ride Ferris wheel in Navy Pier.

What is the best tip for celebrating your anniversary in Chicago?

We have a spa day at The Langrum Hotel to celebrate our anniversary! And Dinner at S.K.Y.

Visited Chicago in August

Photo Shoot Location: Chicago Riverwalk

Lukas in Chicago for Flytographer

Taylor's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

We have a ton of favorites in Chicago, but I have to call out our favorite bar - Lucky Dorr. They helped me with a surprise party post- engagement with our families and friends, and they were the absolute best to work with. If you love good beer, we highly recommend checking them out on your next trip to Wrigley :).

Visited Chicago in August

Photo Shoot Location: Custom Route

Lukas in Chicago for Flytographer

Marianna's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

RPM Italian had amazing, authentic Italian dishes with a unique spin. The homemade pasta was delicious and the bruschetta was some of the best we've ever had! The restaurant has a fun atmosphere and is a great spot for a celebration.

What are the best things to do in Chicago?

The Navy Pier, 360 Chicago, and the Art Institute

What is the best tip for celebrating your anniversary in Chicago?

Make the most of the city views by going to a rooftop bar- like the Roof at the Wit Hotel or the bar at 360 Chicago on the 94th floor. Be sure to tell people when you go out to dinner that you're celebrating your anniversary because you might get a fun dessert on the house (like we did at the Capital Grille!). The Riverwalk is a romantic spot to walk and admire the beautiful city. Chicago has so much to offer, and we'd highly recommend it as an anniversary destination!

Visited Chicago in August

Photo Shoot Location: Custom Route

Monica in Chicago for Flytographer

megan's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

I have a blog featuring all sorts of suggestions! https://www.traverse-blog.com/category/north-america/us-travel/chicago/

What are the best things to do in Chicago?

Chicago is all about the neighborhoods!

Hometown Shoot in June

Photo Shoot Location: Custom Route

Danielle in Chicago for Flytographer

Laurie's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

Gino’s East Pizza - delicious, fun atmosphere, unique deep dish (Buffalo chicken, burger) Nandos - good, quick service, chain unavailable in my home location

What are the best things to do in Chicago?

Museum of Science and Industry, Field Museum, Skydeck/The Ledge

Visited Chicago in June

Photo Shoot Location: The Bean at Millennium Park

Joe in Chicago for Flytographer

Liz's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

Little Goat Diner

What are the best things to do in Chicago?

Lakefront trail, Field Museum, architecture boat tour

Hometown Shoot in June

Photo Shoot Location: North Avenue Beach & Lincoln Park

Joe in Chicago for Flytographer

Christopher's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

Sushi San! We went there after the proposal. Food, drink, and staff were all phenomenal.

What are the best things to do in Chicago?

Architecture tour, Second City improv, and Old Town Ale House

Visited Chicago in May

Photo Shoot Location: Chicago Riverwalk

Joe in Chicago for Flytographer

Laurie's Travel Tips for Chicago

What are the best places to eat and drink in Chicago?

Pequod's for authentic Chicago deep dish pizza

What are the best things to do in Chicago?

Millennium Park

What is your best overall travel tip for Chicago?

Get the Ventra card for public transportation - it's fast and easy, and makes you feel like a local

Visited Chicago in March

Photo Shoot Location: The Bean at Millennium Park

Joe in Chicago for Flytographer

Pam's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

We love the Gold Coast, and also enjoyed a delicious dinner at Mastro’s steakhouse and drinks with a fabulous atmosphere at RPM Italian.

Visited Chicago in February

Photo Shoot Location: Chicago Riverwalk

Adam in Chicago for Flytographer

Cassie's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

Ann Sather and Firecakes Donuts are highly recommended! The architecture boat tour is also a great way to see the city!

Visited Chicago in February

Photo Shoot Location: The Bean at Millennium Park

Monica in Chicago for Flytographer

Nikita's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

Jackets and boots for the winter! Not only do you need them, they look great too :) And if you don’t have them, buy some from Chicago! This city knows its winter fashion.

Visited Chicago in January

Photo Shoot Location: Custom Route

Francisco in Chicago for Flytographer

Morgan's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

Take an architectural river tour!

Visited Chicago in June

Photo Shoot Location: Chicago Riverwalk

Joe in Chicago for Flytographer

Robert's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

Visit Chicago around the Holidays- Yes, it is a tad cold. BUT the hotels were rather inexpensive and the Wrigleyville Christmas Bars were absolutely perfection!

Visited Chicago in December

Photo Shoot Location: Chicago Riverwalk

Joe in Chicago for Flytographer

Jami's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

Eat and see and do all the things!

Visited Chicago in November

Photo Shoot Location: The Magnificant Mile & Chicago Riverwalk

Michael in Chicago for Flytographer

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