What to Do in Chicago
There's much to see and do in Chicago, from checking out artworks by the Grand Masters to soaking up surreal architecture and savoring legendary food. The nightlife is more than just nightclubs – head out to see for yourself!
Weekend Getaway in Chicago: find your perfect rental from just $84 per night!
There's much to see and do in Chicago, from checking out artworks by the Grand Masters to soaking up surreal architecture and savoring legendary food. The nightlife is more than just nightclubs – head out to see for yourself!
A great place to start your weekend is at the Museum Campus, which houses the Adler Planetarium, the Field Museum, and the Shedd Aquarium, all within walking distance of each other. The Museum of Science and Industry (or MSI) is the western hemisphere's largest museum, while Chicago’s Museum of Contemporary Art and Art Institute are home to works by heavyweights such as Warhol and Monet.
In Chicago, centuries-old architectural styles meet futuristic designs. The architecture cruise along the Chicago River introduces you to all styles: Art Deco, neoclassical, Gothic, and of course, towering steel skyscrapers. Learn all about Chicago's skyline with specialist guides.
Try classic deep-dish Chicago pizza with a buttery crust and topped with melted cheese, or a Chicago Italian beef sandwich – it can be ordered dry, wet, or dripping wet! Another must for gastronomes is the Chicago hot dog, a Viennese sausage stuffed into a poppy seed bun. The best are rumored to be Portillo's. Feeling adventurous? Try Malört, a wormwood-based drink brought to Chicago in the 1930s by a Swedish immigrant.
Swing by the Green Mill (opened as Pop Morse's Roadhouse in 1907), a late-night jazz club that was patronized by gangster Al Capone. Marvel at the city's skyline from SkyDeck Chicago and the John Hancock 360 Observatory, or just take an evening helicopter tour. The Chicago Riverwalk makes for a romantic stroll, as does the eco-friendly Chicago Segway Night Tour, which glides by prominent illuminated landmarks.
You'll soon notice that Chicago is a great launching point for day trips to neighboring states, thanks to its excellent transport connectivity and strategic location. Take your pick from sleepy riverside towns and European-style communities right in America.
Less than two hours away from Chicago is Milwaukee, hailed for its German brewing prowess and farm-to-table restaurants. The City of Festivals is also home to the world's only Harley Davidson Museum and over 75 golf courses.
Can't visit the Netherlands? No problem, drive to this Holland to experience Dutch heritage. Top attractions include the Veldheer Tulip Gardens and Windmill Island Gardens. The Dutch architecture, cuisine, and ubiquitous windmills make for Instagram-worthy pictures.
Less than three hours away from Chicago, this 30,000-acre forest offers opportunities for horse riding, hiking and mountain biking, skiing, and snowshoeing. Look out for historical sites such as Old World Wisconsin Outdoor Museum, Wade House Stagecoach Inn, and Holy Hill Basilica.
You've seen Holland, now make way for Switzerland in this Wisconsin city one hour and 40 minutes from Chicago. Cycle along the picturesque, windswept Lake Geneva Shore Path and check out the eclectic nightlife options, restaurants, and independently owned shops.
Nestled along the Illinois-Michigan canal and Illinois River, this bucolic river town is all about antique and collectible shops, wineries, flea markets, and pottery studios. Trace the town's eventful history at the LaSalle County Historical Museum.
What you pack will depend on the season you plan to visit. It goes without saying that a light jacket will always come in handy in the Windy City.
Chances are you'll be bar hopping, attending a Broadway show, or listening to extended blues sessions at a nightclub. Dress the part and fit in with the crowd for a fun time. A denim jacket, jeans, and dressy shoes are a great idea.
The sun shines brightly in Chicago, but sunscreen, good quality sunglasses, and a wide-brim hat will protect you. A refillable water bottle is recommended to keep from being dehydrated.
You'll need a comfy pair of shoes for all those hours spent in museums, parks, and at the clubs. Those planning day trips that involve swimming or hiking should bring along appropriate footwear and a swimsuit.
Bring layers along. A light jacket and shawl will do in the warmer months. Meanwhile, winters demand something heavier, such as a down jacket, thermal underclothes, warm socks, and a wool hat.
📏 Average home size | 91 m² |
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🥳 Busiest month | December |
🛏️ Popular home types | House rental and Apartment rental |
🌡️ Hottest months | July and August |
❄️ Coldest months | 17 °F in January and February |
🌧️ Rainiest months | March and April |
HomeToGo offers incredible vacation rentals, with rates as low as $84 per night.
Apartment rental in Chicago can fit 5 guests.
There are more than 11,200 city break accommodations available in Chicago with prices starting at $84 per night.
There are 2,368 Apartment rentals and 651 House rentals available in Chicago.
The cost of a vacation home in Chicago for the weekend can start from $84 and can go up to $752 per night.
Yes, over 23% accommodations in Chicago come with a pool.