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Family Vacation in Chicago

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Family Vacation in Chicago: Recommended rentals

Family Vacation in Chicago: find your perfect rental from just $66 per night!

Apartment Rush & Division
Apr 1 - Apr 8
Apartment ∙ 7 guests ∙ 3 bedrooms

Family-friendly rental apartment with terrace | Close to John Hancock Center | City view

Rush & Division, Chicago, Illinois, United States
$467
per night
Outstanding(7 ratings)
$467
per night
View deal
House West Loop
Aug 3 - Aug 10
House ∙ 9 guests ∙ 3 bedrooms

Family-friendly vacation home with barbecue | City view | Pets allowed

West Loop, Chicago, Illinois, United States
$388
per night
Excellent(68 ratings)
$388
per night
View deal
Condo Lincoln Park
Mar 18 - Mar 25
Condo ∙ 8 guests ∙ 5 bedrooms

Family-friendly condo with garden & patio

Lincoln Park, Chicago, Illinois, United States
$506
per night
Outstanding(37 ratings)
$506
per night
View deal
Apartment Rush & Division
Jul 6 - Jul 13
Apartment ∙ 10 guests ∙ 4 bedrooms

Family-friendly wonderful apartment with terrace, pool & barbeque | Near John Hancock Center | City view | Beach nearby | Good for workation | Pets are welcome

Rush & Division, Chicago, Illinois, United States
$876
per night
Outstanding(9 ratings)
$876
per night
View deal
Apartment Near North
Mar 18 - Mar 25
Apartment ∙ 7 guests ∙ 2 bedrooms

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

Near North, Chicago, Illinois, United States
$142
per night
Good(22 ratings)
$142
per night
View deal
Apartment Wicker Park
-41%
Jun 1 - Jun 8
Apartment ∙ 8 guests ∙ 3 bedrooms

Apartment | Good for workation

Wicker Park, Chicago, Illinois, United States
$573$420
per night
Excellent(4 ratings)
$573$420
per night
View deal
House Avalon Park
Jun 21 - Jun 28
House ∙ 10 guests ∙ 5 bedrooms

Children-friendly vacation home | Suitable for remote work

Avalon Park, Chicago, Illinois, United States
$469
per night
Outstanding(1 rating)
$469
per night
View deal
Apartment Heart of Chicago
Jul 5 - Jul 12
Apartment ∙ 8 guests ∙ 2 bedrooms

Holiday apartment with patio, grill & hot tub

Heart of Chicago, Chicago, Illinois, United States
$182
per night
Outstanding(5 ratings)
$182
per night
View deal
Condo East Village
Jul 5 - Jul 12
Condo ∙ 7 guests ∙ 3 bedrooms

Condo with patio & BBQ | Suitable for remote work

East Village, Chicago, Illinois, United States
$634
per night
$634
per night
View deal
Condo Rogers Park
Aug 9 - Aug 16
Condo ∙ 8 guests ∙ 4 bedrooms

Fully equipped condo with garden, barbeque & jacuzzi | Nature view | Pets are welcome

Rogers Park, Chicago, Illinois, United States
$297
per night
Outstanding(246 ratings)
$297
per night
View deal
Apartment Streeterville
Mar 18 - Mar 25
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment with terrace | Near John Hancock Center | City view | Good for workation

Streeterville, Chicago, Illinois, United States
$309
per night
Excellent(38 ratings)
$309
per night
View deal
Apartment Logan Square
Apr 1 - Apr 8
Apartment ∙ 4 guests ∙ 3 bedrooms

Beautiful apartment | Pets allowed

Logan Square, Chicago, Illinois, United States
$128
per night
Outstanding(8 ratings)
$128
per night
View deal
Apartment South Loop
Apr 13 - Apr 20
Apartment ∙ 16 guests ∙ 2 bedrooms

Rental apartment with 2 rooms for 16 persons

South Loop, Chicago, Illinois, United States
$738
per night
Outstanding(2 ratings)
$738
per night
View deal
Condo Wrigleyville
Aug 8 - Aug 15
Condo ∙ 9 guests ∙ 4 bedrooms

Condo | Pet-friendly

Wrigleyville, Chicago, Illinois, United States
$592
per night
$592
per night
View deal
House Belmont Central
Jun 30 - Jul 7
House ∙ 16 guests ∙ 7 bedrooms

House with 7 rooms for 16 persons

Belmont Central, Chicago, Illinois, United States
$477
per night
Outstanding(7 ratings)
$477
per night
View deal

Discover the Windy City's Attractions with a Family Vacation in Chicago

Perched on breathtaking Lake Michigan, Chicago is renowned for its spectacular skyline, highlighted by towering skyscrapers with bold architectural designs. The Willis and Tribune Towers are some notable iconic structures. The city ranks among the top kid-friendly destinations in Illinois, thanks to its museums, beautiful gardens, cultural destinations, parks, and plenty of hiking opportunities.
Must-See Family Attractions in Chicago

Must-See Family Attractions in Chicago

A family vacation in Chicago offers plenty of recreational activities and attractions in the downtown area. Here, there's a plethora of cultural centers and opportunities to ride a Ferris wheel. The restaurants lining the city streets serve mouth-watering, children-friendly menus to replenish your energy stores after a day's excursion.

  • 1. Chicago Botanical Garden

    Scenery seekers and nature lovers will love the Chicago Botanical Garden. Set on 385 acres, this beautiful plot features 27 distinct gardens with miniature representations of colorful towns. The Nature Play Garden and its gentle short hills landscape are perfect for kids who love climbing. The Japanese Garden lets you relax in a serene setting with ponds dotted with lilies under curved bridges.

  • 2. Illinois Holocaust Museum & Education Center

    This museum is a valuable resource regarding both WWII history as well as the history of early Jewish immigration to the U.S. The museum features an extensive collection of visual art exhibits and interesting artifacts. The Harvey L. Miller Family Youth Exhibition welcomes 8 to 12-year-olds for hands-on experiences during which they gain useful insights on leadership and how to nurture positive self-esteem.

  • 3. 606 Trail

    A relatively new park in the Windy City, the 606 Trail is a result of the reclamation of a once abandoned railroad. Stretching along Bloomingdale Ave., this path attracts cyclists and walkers to its gentle curves circling well-manicured lawns. As you either walk or cycle, you'll see splendid pieces of art and other sights, including unique flowers and the Exelon Observatory, where visitors enjoy panoramic sunset views, punctuated by the city skyline.

  • 4. Peggy Notebaert Nature Museum

    This museum in Lincoln Park appeals to both history and nature fans. To educate visitors about the natural history of Chicago, the museum uses a collection of hands-on displays. Enter the butterfly greenhouse and revel in magnificent colors or visit the turtle hatcheries and learn how these gentle creatures reproduce and develop until they can forage for themselves.

  • 5. Millennium Park Campus

    This one-of-a-kind park is a must-do for a quintessential Chicago experience. Millennium Park offers free entertainment in the form of outdoor movie screenings, live performances, and exciting festivals. A must-see is The Bean, a cloud-shaped stainless-steel sculpture that reflects the bold skyline. Bring a camera along, as this massive attraction is worth a picture.

Best Places to Stay for Family Vacation in Chicago

Apartment North Center
Sep 19 - Sep 26
-26%
$631
$239
per night
Apartment ∙ 6 guests ∙ 5 bedrooms

Fully equipped wonderful apartment with grill, terrace & garden

5.0
Outstanding(13 ratings)
North Center, Chicago, Illinois, United States
View deal
House South Deering
Jun 28 - Jul 5
$289
per night
House ∙ 8 guests ∙ 4 bedrooms

House with garden | Suitable for remote work

5.0
Outstanding(1 rating)
South Deering, Chicago, Illinois, United States
View deal
House West Chesterfield
Aug 2 - Aug 9
$226
per night
House ∙ 10 guests ∙ 5 bedrooms

House with hot tub

West Chesterfield, Chicago, Illinois, United States
View deal

Information about Family Vacation in Chicago

📏 Average home size 92 m²
😎 Least busy month March
🛏️ Popular home types House rental and Apartment rental
🌡️ Hottest months 84 °F in July and August
❄️ Coldest months 17 °F in January and February
🌧️ Rainiest months March and April

Family Vacation in Chicago: frequently asked questions

Family Vacation in Chicago: What is the price per night for a stay?

On average, you can get a great vacation rental from $133 and find discounts up to 47%!

Family Vacation in Chicago: does HomeToGo offer a wide variety of vacation homes for groups?

Apartment rental in Chicago fits 5 people.

How many family house rentals are available to book in Chicago?

You can find more than 11,235 family accommodations in Chicago with nightly prices starting from $66 per night.

Family Vacation in Chicago: what kinds of vacation rentals can I book in Chicago?

We would suggest checking out our selection of House rentals and Apartment rentals in Chicago.

How much does a family house cost to rent in Chicago?

The price of a large vacation rental in Chicago can range from $133 and can go up to $719 per night during the busy season in October.

Can you book family-sized accommodations in Chicago include a pool?

Of course, over 23% of family vacation rentals in Chicago come with a pool.

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

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Vacation rentals near Chicago with popular amenities

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Check out vacation rentals with popular amenities in Chicago

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