Curator’s statement
Chicago is my favorite city. I loved to visit so much that I spent years trying to move here, and now I've lived here for six years! Each area of the city has a unique vibrant culture and feel, but the city is easier to explore than New York or LA because it's smaller and still very accessible. Chicago has everything you could want — incredible food, unique attractions and a gorgeous shoreline.
The Fora Difference
Book with Courtney to access exclusive perks and experiences on your trip.
Killer perks
Free upgrades, spa credits and more—we got you
Personalized recs
Customized travel planning for your style
Insider knowledge
Expert advice from people who’ve actually been there
Where to stay in Chicago
Four Seasons Hotel Chicago
Best-of-the-best on the Magnificent Mile, with standout service and unmatched views of Lake Michigan and the cityscape.
Fora Perks
- ★
$100 food / beverage or spa credit.
- ★
Breakfast daily.
- ★
Upgrade whenever possible.
The Langham, Chicago
A Chicago icon set apart by its Mies van der Rohe-designed building, Chicago River and city views, and sleek mid-century style.
Fora Perks
- ★
$100 hotel / resort credit.
- ★
Breakfast daily.
- ★
Upgrade & extended check-in/out whenever possible.
Chicago Athletic Association
Chic hotel with a fun vintage sports theme set in a historic building overlooking Chicago's Millennium Park.
Fora Perks
- ★
Hotel / resort credit.
- ★
Welcome amenity.
- ★
Breakfast daily.
- ★
Upgrade & extended check-in/out whenever possible.
The Robey
A hip pick in two landmark buildings in Wicker Park, with unique bunk and loft rooms that groups love.
Fora Perks
- ★
Breakfast daily.
- ★
Upgrade & extended check-in/out whenever possible.
The Hoxton, Chicago
As much about the play as the stay, this Fulton Market favorite has a hotspot restaurant, bar and rooftop pool, plus supremely comfortable bedrooms.
Unlock perks by contacting Courtney to book your trip.
Things to do in Chicago
Parks
Millennium Park - You can't come to Chicago and not head to the famous cloud gate (the bean) to take a selfie. Pro tip: Head to the bean at sunrise for incredible solo pics! After you snap your perfect picture, wander around the park. In the summer, bring a picnic and catch a free concert Mondays and Thursdays evenings and a free movie on Tuesday evenings!
Lincoln Park Zoo - The zoo is free to visit and see the animals and you can spend an entire day exploring all of the exhibits. Pro tip: Don't forget to check out the Alfred Caldwell Lily Pond for a tranquil and secluded experience — its lush green landscape won't disappoint.
Museums
Field Museum - The Field Museum is my favorite museum to visit and I could go there again and again and always learn something new. I love to explore the different exhibits and you could easily spend an entire day on your visit. Pro tip: Purchase your tickets in advance to skip the line — they get long in the summer. See the largest and best-preserved T-Rex ever found (Sue) on the upper level! After your Field Museum visit, head over the Shedd Aquarium to visit the adorable penguins.
The Art Institute of Chicago - The art institute houses some of the most famous and recognizable art pieces and many don't often realize it — see Van Gogh's self-portrait and American Gothic. Pro tip: Recreate the scene from Ferris Bueller's Day Off and snap some pictures to prove it.
Activities
See the Cubs play at Wrigley Field - If you're in Chicago during baseball season, snag a ticket to see the Cubs play and don't forget to take a picture of the sign on the corner of Clark and Addison. Pro tip: Avoid the crazy Wrigleyville bar scene and walk five minutes over to Southport Corridor for a pre- or post-game meal.
Go antique shopping in Andersonville - Head up north to one of Chicago's best-kept secrets and visit Andersonville, voted Time Out's 2021 Coolest Neighborhood in America and second Coolest Neighborhood in the World. The neighborhood is filled with local shops and eateries and is a hot spot for local antique shoppers. Pro tip: Shop on Clark Street and then head to Hopleaf to sit on the back patio for a burger and Belgian beer. If you're visiting in the winter, head to Simon's for some glogg!
Visit one of Chicago's "third coast" beaches - Tune out the noise of the city, pop on a bathing suit and head over to one of Chicago's beaches to feel like you've escaped to a totally different destination. Most of the beaches have snack bars or restaurants to grab a quick bite or drink. Pro tip: Head up north to Montrose, Foster or Kathy Osterman Beach to miss the North Ave and Oak Street Beach crowds and actually have room for your towel.
Tours
Architecture boat tour - Hop on a boat and float down the river while learning about Chicago's iconic architecture. This tour is a favorite of locals and tourists. Pro tip: Skip crowded City Winery and head over to The Northman instead after your tour for a quick drink or bite to eat.
Places to eat & drink in Chicago
West Loop
Cabra - Cabra, located on the rooftop of the Hoxton, has a very unique and playful menu. If you're a fan of Top Chef, this restaurant is one of Stephanie Izard's restaurants in the city. The atmosphere is colorful with beautiful views, and I highly recommend any of the ceviches or dips! Pro tip: Visit in warm weather for beautiful open-air seating on the roof.
Au Cheval - Au Cheval has what many consider the best burger in the city. They keep it simple with a classic single or double cheeseburger, and you can add on an egg or bacon! Pro tip: They do not offer reservations, so snag your food to go or head to one of their satellite Small Cheval locations if you're in a rush.
Green Street Smoked Meats - Having lived in the South, I was skeptical of Chicago barbecue, but Green Street Smoked Meats doesn't miss. Don't forget to get the sides — the elote is the best I've ever had. Pro tip: Go early! They run out of certain dishes later in the day.
Trivoli Tavern - After you've visited Green Street Meats, continue down the alley to Trivoli Tavern. This Italian restaurant feels like a speakeasy and has fantastic meat and handmade pasta dishes (try the alla vodka!), drinks and a really cool atmosphere. Pro tip: Go from 4-5 pm for happy hour and Wednesday evenings for half-price bottles of wine.
Duck Duck Goat - Another one of Stephanie Izard's restaurants, Duck Duck Goat offers a unique take on Chinese American cuisine. The duck fried rice is my favorite dish on the menu — at brunch, you can even get it wrapped in an omelet. Pro tip: After your meal, head around the corner to Baobing Bar when it's open for soft serve sundaes and some additional food to take home.
Andersonville
Hopleaf - Featured on Diners, Drive-Ins and Dives, Hopleaf has a diverse and seasonal menu with a huge selection of beer. Pro tip: Ask to be seated on the patio if it's a warm day to feel like you've escaped the busy Chicago city.
Big Jones - Grab a bite at Big Jones for a new twist on traditional Southern dishes from a chef that has beat Bobby Flay. Located in Andersonville, this small restaurant is a perfect stop as you explore a new part of the city. Pro tip: If you visit during brunch, you can try the Beat Bobby Flay biscuit sandwich — it doesn't disappoint.
Lost Larson - With two locations, one in Wicker Park and one in Andersonville, Lost Larson is a must-stop for coffee and delicious flaky pastries. Pro tip: Another great patio in the summer, grab your coffee and head out the side door to eat and drink out back on their patio.
Lincoln Park
Boka - Boka has one Michelin star and it is very well deserved. Boka is my favorite restaurant in the city and I could eat there almost every day (I wish)! They have a great variety of seasonal American dishes, delicious cocktails and a cool atmosphere. Pro tip: Visit during Restaurant Week for a great deal on their tasting menu.
Pequod's - Skip the typical Giordano's or Lou Malnati's and hit up Pequod's for the best deep-dish pizza in the city. Pro tip: Hit up the weekday lunch special for the best deal.
![Advisor - Courtney Johnson](https://media.foratravel.com/image/upload/v1711124023/contentful-migration/advisors/image/courtney-johnson.jpg)
Travel Advisor
Courtney Johnson
Get in touch with Courtney
Did you like this guide? Reach out to customize and book your own experience. Or, just to chat about travel in general.
You can normally expect a response from Courtney within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).
Looking for more inspiration? Check out my guide, Maui, Hawai'i: A Guide to Your Tropical Adventure.
This guide is part of our ongoing series on travel to Chicago.