Curator’s statement
Chicago - The beloved unofficial capital of the Midwest is a bustling metropolis set against the beautiful Lake Michigan. This city offers endless activities, world-class dining and incredibly friendly hospitality. Although the winters bring its nickname The Windy City to life, there is nothing quite like the vibrancy and spirit of Summertime Chi. Having visited family and friends there for the last 15 years, I have compiled some of my recommendations below.
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Where to stay in Chicago
Thompson Chicago
Experience contemporary elegance and world-class hospitality at Thompson Chicago, a Hyatt-affiliated hotel blending sophistication, modern design, and exceptional amenities in the heart of the city.
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Hotel / resort credit.
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Welcome amenity.
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Breakfast daily.
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Upgrade & extended check-in/out, whenever possible.
Fairmont Chicago Millennium Park
Where modern luxury meets classic elegance, offering unparalleled views and exceptional hospitality in the heart of the Windy City.
Fora Perks
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Breakfast daily.
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Upgrade & extended check-in/out whenever possible.
Pendry Chicago
A contemporary luxury hotel is set within the iconic 1929 Art Deco Carbide & Carbon Building in Chicago’s Loop neighborhood.
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$100 hotel credit.
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Breakfast daily.
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Upgrade & extended check-in/out whenever possible.
Freehand Chicago
This stylish Freehand outpost is housed in a classic 1927 building in Chicago’s vibrant and artistic River North neighborhood.
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.
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Things to do in Chicago
Lake Michigan — What’s better than being on the water in the heat of summer? Rent a boat, kayak or jet-ski to enjoy the beautiful lake and views of the city skyline.
Street Festivals — Chicago truly comes alive in the summertime. Watch the US Navy Blue Angels perform incredible stunts at the Annual Air & Water Show, a tradition unlike any other. Be sure to also check out the extensive festival schedule across the city, full of live music, food and antiques.
Ride bikes — Take a leisure ride along the 19-mile-long Lakefront Trail while admiring the beautiful views of the city and Lake Michigan.
River boat tour — Sit back and relax while cruising Chicago’s 3 river branches while hearing about its history and architecture.
Catch a show — There are countless music, theater and comedy venues all around the city. From stadiums and arenas to smaller intimate theaters across the city, there are so many options to choose from. City Winery is one of my favorite spots.
Enjoy al fresco happy hour — What better way to people-watch than to enjoy an ice-cold beverage outdoors? Whether you are in the mood for a cocktail at a swanky rooftop lounge, or a local Goose Island draft beer at a water-side cafe, there is somewhere for everyone.
Catch a game — Chicago fans love their sports. Visit the infamous Wrigley Field for a Cubs game, the United Center for a Bulls or Blackhawks game or Soldier Field for a Bears game.
Sites & Museums — If you’re not afraid of heights, step out on The Ledge at the Skydeck of the Sears Tower (now known as Willis Tower, but no one calls it that…). If you prefer to stay on ground level, check out The Bean in Millennium Park or the Ferris Wheel at Navy Pier. There is also no shortage of incredible museums — whether you are into architecture, art or history, there is something to pique everyone’s interest.
Day Trips:
Chicago can serve as a great home base for many single- or multi-day trips that are within a three-hour drive or a quick flight!
Madison, WI
Indianapolis, IN
St. Louis, MO
Minneapolis, MN
Places to eat & drink in Chicago
BRUNCH/LUNCH
Firecakes Donuts (River North) - Small-batch artisan donuts — they sell out early!
Beatrix (various locations) - The menu features healthy-meets-delicious specials and is known for its in-house bakery and coffee bar, including signature cookies and baked goods.
Cira (West Loop) - Modern Mediterranean restaurant celebrating fresh, coastal ingredients.
Hampton Social (River North) - Coastal-inspired food, cocktails and live music in a beautifully designed space.
Avli (River North) - Modern Greek restaurant offering contemporary Greek cuisine in a fun & festive atmosphere with a great outdoor patio.
Giordano’s or Gino’s (various locations) - Traditional deep-dish style pizza in casual settings
DINNER
Dawson (River West) - Globally-inspired American cuisine with the season's finest ingredients.
The Publican (Fulton Market) - A creative seafood & pork-focused menu plus global brews in a hip setting with communal tables.
Girl & The Goat (Fulton Market) - Serving bold, global flavors, cocktails, wine and locally-rooted beer.
Brasero (West Town) - New South American restaurant serving meats and other items kissed by the grill or the wood-fired oven.
Sunda (River North) - A hip spot for creative Asian fusion fare, sushi & specialty cocktails in a chic modern space.
Jaleo (River North) - Jaleo brings alive the spirit and flavors of Spain through a traditional and cutting-edge tapas experience.
Roka Akor (River North) - Upscale Japanese restaurant & bar supplying steak, seafood & sushi in a contemporary setting.
HAPPY HOUR & AFTER-DINNER DRINKS
Cindy’s (Millennium Park) - The rooftop restaurant and bar at the Chicago Athletic Association Hotel offers unparalleled views of the city.
Z Bar (Magnificent Mile) - Peninsula Hotel rooftop.
Dorian’s (Wicker Park) - Through a door at the back of its listening room is a lounge area with tables, comfy booths and a small stage.
Centennial Craft Beer & Eatery (River North)
Northman Beer & Cider Garden (Riverwalk)
City Winery (Riverwalk)
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Travel Advisor
Alexandra Gonzalez
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This guide is part of our ongoing series on travel to Chicago. Looking for more travel inspiration? Check out my guide, A First-Timer’s Guide to 5 Days in London.