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Family Vacation in Chicago

Chicago
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Distance to center
Max. 1 mi
Max. 2 mi
Max. 3 mi
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

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.

Family Vacation in Chicago: Top Accommodations

Apartment South Loop
Jan 22 - Jan 29
-56%
$503
$223 per night
Apartment ∙ 3 guests ∙ 1 bedroom
3.8
"Good" (57 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Details
travelstaytion
View deal
Apartment South Loop
Jan 22 - Jan 29
-64%
$465
$166 per night
Apartment ∙ 2 guests ∙ 1 bedroom
3.8
"Good" (76 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Details
travelstaytion
View deal
Apartment South Loop
Jan 28 - Feb 4
-72%
$604
$172 per night
Apartment ∙ 3 guests ∙ 1 bedroom
3.8
"Good" (91 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Details
travelstaytion
View deal

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.

  • 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.

  • 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.

  • 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.

  • 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.

  • 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 South Loop
Jan 28 - Feb 4
-70%
$739
$225 per night
Apartment ∙ 3 guests ∙ 1 bedroom
3.8
"Good" (48 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Details
travelstaytion
View deal
Apartment South Loop
Jan 14 - Jan 21
-70%
$526
$159 per night
Apartment ∙ 3 guests ∙ 1 bedroom
South Loop, Chicago, Illinois, United States
Details
Kasa Living
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Apartment South Loop
Jan 22 - Jan 29
-64%
$465
$166 per night
Apartment ∙ 2 guests ∙ 1 bedroom
3.8
"Good" (16 ratings)
South Loop, Chicago, Illinois, United States
Free cancellation
Details
travelstaytion
View deal

Frequently Asked Questions

How much do vacation rentals for Family Vacation in Chicago cost?

On average, you can get an incredible rental for somewhere between $184 and $419 and find discounts up to 63%!

What kinds of rentals can I find for Family Vacation in Chicago?

You can find 520 Apartment rentals and 67 Bed & Breakfast rentals for Family Vacation in Chicago right here on HomeToGo.

The Weather in Chicago

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Average Nightly Rental Prices in Chicago

Vacation Rental Price Information in Chicago

Vacation Rental Availability in Chicago

Rental Availability Information in Chicago

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