Top Destinations for a Weekend Getaway in Chicago - HomeToGo base64Hash Top Destinations for a Weekend Getaway in Chicago - HomeToGo

Top Destinations for a Weekend Getaway in Chicago

Chicago
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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.

City Breaks in Chicago: Top Accommodations

Apartment South Loop
$176 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment Near North
$192 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Near North, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment Near North
$110 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Details
Kasa Living
View deal
What to Do in Chicago base64Hash What to Do in Chicago

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!

  • 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.

  • 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.

  • 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.

  • 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.

City Breaks in Chicago: Top Accommodations

Apartment South Loop
$176 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment South Loop
$118 per night
Apartment ∙ 2 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment Near North
$114 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Details
Kasa Living
View deal
Day Trips from Chicago base64Hash Day Trips from 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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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.

City Breaks in Chicago: Top Accommodations

Apartment Near North
$192 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Near North, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment South Loop
$146 per night
Apartment ∙ 3 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment South Loop
$176 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
What to Pack for Your Weekend Getaway in Chicago base64Hash What to Pack for Your Weekend Getaway 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.

  • 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.

  • 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.

  • 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.

  • 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.

City Breaks in Chicago: Top Accommodations

Apartment South Loop
$176 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment South Loop
$118 per night
Apartment ∙ 2 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Details
Kasa Living
View deal
Apartment Near North
$114 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Near North, Chicago, Illinois, United States
Details
Kasa Living
View deal

What kind of prices can I expect when planning Weekend Getaway in Chicago?

The average price for accommodation in Chicago is between usually $163 and $365 per night.

What kinds of rentals can I find for Weekend Getaway in Chicago?

We would suggest browsing our an incredible selection of available Hotel rooms and Apartment rentals to complete your Weekend Getaway in Chicago.

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