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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Weekend Getaway in Chicago: Recommended rentals

Weekend Getaway in Chicago: find your perfect rental from just $84 per night!

House Old Town
Jul 26 - Aug 2
House ∙ 12 guests ∙ 7 bedrooms

House with Sauna, Yard & Patio | City View

Old Town, Chicago, Illinois, United States
$1,575
per night
Outstanding(71 ratings)
$1,575
per night
View deal
House Douglas
-49%
Apr 7 - Apr 14
House ∙ 6 guests ∙ 3 bedrooms

Nice House with Garden | Suitable for Remote Work

Douglas, Chicago, Illinois, United States
$479$100
per night
$479$100
per night
View deal
House South Deering
Mar 3 - Mar 10
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home with Garden | Perfect for Remote Work

South Deering, Chicago, Illinois, United States
$182
per night
Outstanding(1 rating)
$182
per night
View deal
Apartment Rush & Division
Mar 3 - Mar 10
Apartment ∙ 7 guests ∙ 3 bedrooms

Family-Friendly Rental Apartment with Terrace | Near John Hancock Center | City View

Rush & Division, Chicago, Illinois, United States
$575
per night
Outstanding(6 ratings)
$575
per night
View deal
House River West
Feb 16 - Feb 23
House ∙ 11 guests ∙ 4 bedrooms

House with Terrace, BBQ & Garden | City View | Suitable for Remote Work

River West, Chicago, Illinois, United States
$536
per night
Outstanding(98 ratings)
$536
per night
View deal
Apartment Grand Boulevard
-44%
Feb 22 - Mar 1
Apartment ∙ 6 guests ∙ 2 bedrooms

Holiday Apartment with 2 Rooms for 6 Persons

Grand Boulevard, Chicago, Illinois, United States
$246$157
per night
(2 ratings)
$246$157
per night
View deal
Condo Rogers Park
-20%
May 28 - Jun 4
Condo ∙ 6 guests ∙ 3 bedrooms

Condo with Patio | Perfect for Remote Work

Rogers Park, Chicago, Illinois, United States
$309$254
per night
Excellent(23 ratings)
$309$254
per night
View deal
Apartment Washington Park
May 28 - Jun 4
Apartment ∙ 3 guests ∙ 3 bedrooms

Holiday Apartment with Barbeque & Patio | Good for Workation

Washington Park, Chicago, Illinois, United States
$87
per night
$87
per night
View deal
House Lake View
-38%
May 31 - Jun 7
House ∙ 8 guests ∙ 3 bedrooms

House with Barbecue

Lake View, Chicago, Illinois, United States
$769$281
per night
Outstanding(5 ratings)
$769$281
per night
View deal
House Streeterville
-68%
Feb 16 - Feb 23
House ∙ 4 guests ∙ 1 bedroom

Vacation Home | Close to John Hancock Center | City View

Streeterville, Chicago, Illinois, United States
$366$106
per night
Outstanding(1 rating)
$366$106
per night
View deal
Condo Rogers Park
Aug 4 - Aug 11
Condo ∙ 8 guests ∙ 4 bedrooms

Fully Equipped Condo with BBQ, Yard & Jacuzzi | Nature View | Dogs Allowed

Rogers Park, Chicago, Illinois, United States
$251
per night
Outstanding(243 ratings)
$251
per night
View deal
Apartment South Austin
Mar 3 - Mar 10
Apartment ∙ 6 guests ∙ 3 bedrooms

Holiday Apartment | Suitable for Remote Work

South Austin, Chicago, Illinois, United States
$149
per night
Excellent(34 ratings)
$149
per night
View deal
Apartment Chicago Loop
Jul 19 - Jul 26
Apartment ∙ 8 guests ∙ 4 bedrooms

Family-Friendly Big Holiday Apartment with Terrace & Pool | Next to Cloud Gate | Pets Allowed

Chicago Loop, Chicago, Illinois, United States
$744
per night
Outstanding(35 ratings)
$744
per night
View deal
Apartment Logan Square
Jul 5 - Jul 12
Apartment ∙ 4 guests ∙ 3 bedrooms

Wonderful Holiday Apartment | Pet-Friendly

Logan Square, Chicago, Illinois, United States
$133
per night
Outstanding(8 ratings)
$133
per night
View deal
House Fifth City
-41%
Mar 3 - Mar 10
House ∙ 5 guests ∙ 3 bedrooms

Children-Friendly Beautiful Vacation Home with Garden, Barbeque & Patio | Perfect for Remote Work

Fifth City, Chicago, Illinois, United States
$259$201
per night
Outstanding(18 ratings)
$259$201
per night
View deal

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.
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

House Hyde Park
Feb 25 - Mar 4
$592
per night
House ∙ 8 guests ∙ 5 bedrooms

House with barbeque & yard

5.0
Outstanding(5 ratings)
Hyde Park, Chicago, Illinois, United States
View deal
House Near North Side
Jul 5 - Jul 12
$779
per night
House ∙ 14 guests ∙ 3 bedrooms

Fully equipped house with terrace | City view

4.7
Excellent(27 ratings)
Near North Side, Chicago, Illinois, United States
View deal
Apartment Near North
Jun 21 - Jun 28
$272
per night
Apartment ∙ 7 guests ∙ 2 bedrooms

Holiday apartment with terrace | Near John Hancock Center | City view

3.6
Good(22 ratings)
Near North, Chicago, Illinois, United States
View deal
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

Apartment Streeterville
Feb 22 - Mar 1
-66%
$683
$328
per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment with Terrace | Near John Hancock Center | City View

4.8
Outstanding(57 ratings)
Streeterville, Chicago, Illinois, United States
View deal
House Goose Island
Feb 1 - Feb 8
$209
per night
House ∙ 14 guests ∙ 3 bedrooms

Family-Friendly Big House with Barbeque, Terrace & Sauna | City View | Perfect for Remote Work

5.0
Outstanding(51 ratings)
Goose Island, Chicago, Illinois, United States
View deal
Apartment River North
Feb 26 - Mar 5
$160
per night
Apartment ∙ 5 guests ∙ 2 bedrooms

Apartment | Close to Wrigley Building

River North, Chicago, Illinois, United States
Free cancellation
View deal
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

Condo River North
Jun 7 - Jun 14
-27%
$1,365
$741
per night
Condo ∙ 8 guests ∙ 4 bedrooms

Condo | Near John Hancock Center

5.0
Outstanding(68 ratings)
River North, Chicago, Illinois, United States
View deal
Apartment Chicago Loop
Mar 26 - Apr 2
$522
per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment with Terrace & Pool | Next to Cloud Gate | City View

4.9
Outstanding(50 ratings)
Chicago Loop, Chicago, Illinois, United States
View deal
Condo Pulaski Park
Jul 12 - Jul 19
-18%
$513
$361
per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo with 3 Rooms for 8 Persons

4.4
Very good(10 ratings)
Pulaski Park, West Town, Chicago
View deal

Information about Weekend Getaway in Chicago

📏 Average home size 91 m²
🥳 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

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 $84 per night.

Weekend Getaway in Chicago: can I find a vacation rental suitable for a group?

Apartment rental in Chicago can fit 5 guests.

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

There are more than 11,200 city break accommodations available in Chicago with prices starting at $84 per night.

Weekend Getaway in Chicago: what kinds of vacation rentals can I find in Chicago?

There are 2,368 Apartment rentals and 651 House 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 $84 and can go up to $752 per night.

Do many accommodations in Chicago offer a pool?

Yes, over 23% accommodations in Chicago come with a pool.

Average Nightly Rental Prices in Chicago

Click on any bar to see price and availability information

Vacation Rental Price Information in Chicago

Vacation Rental Availability in Chicago

Rental availability information in Chicago

Check out more vacation options

Check out other vacation accommodation options in Chicago

Vacation rentals near Chicago with popular amenities

Check out vacation rentals with popular amenities in Chicago

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