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

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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 Washington Park
Oct 14 - Oct 21
$99 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Apartment in Washington Park
Washington Park, Chicago, Illinois, United States
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House West Town
Mar 9 - Mar 16
$175 per night
House ∙ 8 guests ∙ 3 bedrooms
Nice House in West Town
4.5
Excellent (14 ratings)
West Town, Chicago, Illinois, United States
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Condo The Gap
Jan 20 - Jan 27
-24%
$124
$95 per night
Condo ∙ 5 guests ∙ 2 bedrooms
Condo in The Gap
3.6
Good (27 ratings)
The Gap, Chicago, Illinois, United States
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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!

  • 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.

  • 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.

  • 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.

  • 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

Apartment Heart of Chicago
Feb 3 - Feb 10
-53%
$208
$98 per night
Apartment ∙ 5 guests ∙ 2 bedrooms
Entire Apartment in Heart Of Chicago
5.0
Outstanding (50 ratings)
Heart of Chicago, Chicago, Illinois, United States
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Apartment Heart of Chicago
Sep 23 - Sep 30
-77%
$534
$126 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Apartment in Heart Of Chicago with Free Parking
4.9
Outstanding (12 ratings)
Heart of Chicago, Chicago, Illinois, United States
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House The Island
Dec 1 - Dec 8
-39%
$171
$105 per night
House ∙ 8 guests ∙ 3 bedrooms
Wonderful Vacation Home in The Island with Yard
4.5
Excellent (14 ratings)
The Island, Chicago, Illinois, United States
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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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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

Condo The Gap
Jan 20 - Jan 27
-24%
$124
$95 per night
Condo ∙ 5 guests ∙ 2 bedrooms
Condo in The Gap
3.6
Good (27 ratings)
The Gap, Chicago, Illinois, United States
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House Douglas
Nov 11 - Nov 18
-70%
$452
$137 per night
House ∙ 9 guests ∙ 4 bedrooms
House in Douglas
3.9
Good (21 ratings)
Douglas, Chicago, Illinois, United States
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Apartment Ukrainian Village
Dec 9 - Dec 16
-50%
$798
$397 per night
Apartment ∙ 10 guests ∙ 4 bedrooms
Apartment in Ukrainian Village with Private Balcony + Great View
5.0
Outstanding (4 ratings)
Ukrainian Village, Chicago, Illinois, United States
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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.

  • 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.

  • 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.

  • 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.

  • 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

House Mayfair
Feb 17 - Feb 24
$270 per night
House ∙ 10 guests ∙ 5 bedrooms
Comfortable House in Mayfair with Botanical Garden
4.9
Outstanding (104 ratings)
Mayfair, Chicago, Illinois, United States
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Condo West Ridge
Jun 22 - Jun 29
-26%
$268
$199 per night
Condo ∙ 8 guests ∙ 3 bedrooms
Beautiful Condo in West Ridge with Yard
4.1
Very good (15 ratings)
West Ridge, Chicago, Illinois, United States
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Apartment South Chicago
Jun 15 - Jun 22
-23%
$114
$88 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Wonderful Apartment in South Chicago
4.5
Excellent (4 ratings)
South Chicago, Chicago, Illinois, United States
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Information about Weekend Getaway in Chicago

😎 Least busy month October
🥳 Busiest month August
🛏️ Popular home types House rental and Apartment rental
🌡️ Hottest months 84 °F in July and August
❄️ Coldest months January and February
🌧️ Rainiest months March and April

Frequently Asked Questions

How many vacation homes are available to rent for a weekend in Chicago?

You can find more than 8,630 homes for rent in Chicago with prices starting at $60 per night.

What types of vacation homes can I find for Weekend Getaway in Chicago?

There are many House rental and Apartment rental that are perfect for Weekend Getaway in Chicago.

Weekend Getaway in Chicago: How much does it cost to rent a vacation home in Chicago?

HomeToGo offers great rentals for Weekend Getaway in Chicago, with prices as low as $60 per night.

Can I find a vacation home for a group of guests for Weekend Getaway in Chicago?

Apartment rental in Chicago usually fits 4 guests.

How much does it cost to take a weekend getaway in Chicago?

The price of a rental in Chicago for the weekend can start from $60 and can go up to $509 per night.

Do many vacation rentals in Chicago include a pool?

Absolutely, more than 27% accommodations in Chicago offer a pool.

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Average Nightly Rental Prices in Chicago

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Vacation Rental Price Information in Chicago

Vacation Rental Availability in Chicago

Rental availability information in Chicago

Weekend Getaway in Chicago Inspiration

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