Photograph by: Joe

Best Things to Do in Chicago

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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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


Concepcion's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

Be aware that you will have to walk a lot if you want to explore all the city.

Visited Chicago in November

Photo Shoot Location: Custom Route

David in Chicago for Flytographer


Claire's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

Chicago is an incredibly walkable city! I love that even with the stroller I was able to get anywhere I need to go on foot. And for the rare attractions that were a bit further afield, the transit system was great!

Visited Chicago in November

Photo Shoot Location: Custom Route

Danielle in Chicago for Flytographer


krista's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

Sunday brunch at the Peninsula, Hamilton, and aptitude resting at the Johnson O’Connor research center.

Visited Chicago in November

Photo Shoot Location: Custom Route

Joe in Chicago for Flytographer


Lauren's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

Don't be afraid of public transportation. It's easy, convenient, and pretty quick! Get the Ventra card for easy, unlimited stops.

Visited Chicago in November

Photo Shoot Location: North Avenue Beach

Michael in Chicago for Flytographer


Emily's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

Weekdays at the museum's meant less crowds and more space for my toddlers to roam.

Visited Chicago in October

Photo Shoot Location: The Bean at Millennium Park

Joe in Chicago for Flytographer


Jenny's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

Make sure to take the Architectural Tour from the Architectural Institute. It'll give you an appreciate for the city and the rest of your trip that is unparalleled!

Visited Chicago in November

Photo Shoot Location: Custom Route

Joe in Chicago for Flytographer


karina's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

Levantarse temprano a conocer los lugares mas importantes como TheBean y otros lugares turisticos para que puedan disfrutarlo sin tanto turista y poder tomar unas fotos increibles.

Visited Chicago in August

Photo Shoot Location: Millennium Park & Chicago Riverwalk

Monica in Chicago for Flytographer


Soraya's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

You MUST have breakfast at Yolk! Hands-down, it serves THE best breakfast in the city. Be warned...Sundays the wait can be long but its worth it!

Visited Chicago in May

Photo Shoot Location: The Museum Campus

Michael in Chicago for Flytographer


Abigail's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

A must visit is the road near the planetarium or aquarium. The sidewalk next to the lake has the best view of the city from across the lake. The view of the skyline with the blue of the lake is spectacular.

Visited Chicago in April

Photo Shoot Location: Custom Route

Adam in Chicago for Flytographer


Victoria's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

We absolutely love this city! Try everything! :)

Visited Chicago in August


Elizabeth's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

Definitely have to do a helicopter tour and boat ride down the Riverwalk.

Visited Chicago in October

Photo Shoot Location: Chicago Riverwalk

Lukas in Chicago for Flytographer


erin's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

You must put your feet in Lake Michigan! Try the deep dish pizza! The people in Chicago are friendly. They say hello while out walking! 

Visited Chicago in July

Photo Shoot Location: Millennium Park & Chicago Riverwalk

Michael in Chicago for Flytographer


Alex's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

Get photographs in places that aren't as popular, but still look great on camera!

Visited Chicago in December

Photo Shoot Location: Custom Route

Joe in Chicago for Flytographer


Tracy's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

December may be cold in Chicago... but it's actually a really special time to visit! Many of the stores along the Magnificent Mile are all decorated for Christmas. We visited Santa at Macy's, went ice skating at Millennium Park, and saw the miniature rooms at the Art Institute all decorated for the holidays.

Visited Chicago in December

Photo Shoot Location: The Magnificant Mile & Chicago Riverwalk

Michael in Chicago for Flytographer


Mohamed's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

Favourite Restaurant: Girl and the Goat, Lou Malnati's Favourite Donuts: Glazed and Infused - the Nutella Long John is amazing!

Visited Chicago in December

Photo Shoot Location: Custom Route

Michael in Chicago for Flytographer


Ha's Travel Tips for Chicago

What is your best overall travel tip for Chicago?

Our photographer, Francisco, was wonderful! He was very easy to work with. He listened to what We wanted for our photos. We had great conversations. I highly recommend choosing him for Chicago.

Visited Chicago in November


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