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: Recommended rentals
Weekend Getaway in Chicago: find your perfect rental from just $46 per night!
Planning a Weekend Getaway in Chicago
Famous for its deep-dish pizza and hot dogs, America's Windy City makes for the perfect adventure. Its fantastical architecture, jazz and blues culture, world-class museums, and festivals are second to none. A weekend getaway will prove unforgettable.
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1. Museum hopping
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.
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2. Chicago river boat architecture tour
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.
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3. Signature Chicago food
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.
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4. Nighttime entertainment
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.
Best Places to Stay for City Breaks in Chicago
Day Trips from Chicago
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.
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1. Milwaukee
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.
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2. Holland, Michigan
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.
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3. Kettle Moraine State Forest
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.
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4. Lake Geneva
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.
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5. North Utica
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.
Recommended Accommodations for City Breaks in Chicago
What to Pack for Your Weekend Getaway in Chicago
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.
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1. Smart casual wear
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.
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2. Sun protection
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.
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3. Comfortable walking shoes
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.
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4. Layered clothes
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.
Top Offers for City Breaks in Chicago
Information about Weekend Getaway in Chicago
| 💳 Highest rates | in May |
|---|---|
| 🥳 Busiest month | January |
| 🛏️ Popular home types | Apartment rental and Bed and breakfast rental |
| 🌡️ Hottest months | July and August |
| ❄️ Coldest months | 17 °F in January and February |
| 🌧️ Rainiest months | 9 rainy days in March and April |
54,612 reviews
Chicago vacation rentals have an average rating of 4.4/5 on 54,612 reviews left by travelers.
Weekend Getaway in Chicago: frequently asked questions
Weekend Getaway in Chicago: What is the nightly cost of a stay?
HomeToGo offers incredible vacation rentals, with rates as low as $46 per night.
Weekend Getaway in Chicago: can I find a vacation rental suitable for a group?
Bed and breakfast rental in Chicago can fit 3 guests.
How many vacation homes are available to rent for a weekend in Chicago?
There are more than 5,467 city break accommodations available in Chicago with prices starting at $46 per night.
Weekend Getaway in Chicago: what kinds of vacation rentals can I find in Chicago?
There are 84 Bed and breakfast rentals and 166 Apartment rentals available in Chicago.
How much does it cost to take a weekend getaway in Chicago?
The cost of a vacation home in Chicago for the weekend can start from $46 and can go up to $449 per night.
Do many accommodations in Chicago offer a pool?
Yes, over 33% accommodations in Chicago come with a pool.
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