Book Chicago Family Vacations

Best Kid friendly vacations in Chicago

Residence Inn Chicago Downtown/Loop
Palmer House a Hilton Hotel
Hilton Chicago

Kid friendly vacation packages for 3 nights

Residence Inn Chicago Downtown/Loop
Palmer House a Hilton Hotel
Hilton Chicago

Kid friendly vacation packages for 4 nights

Residence Inn Chicago Downtown/Loop
Hilton Chicago
Palmer House a Hilton Hotel

Kid friendly vacation packages for 5 nights

DoubleTree by Hilton Chicago - Magnificent Mile
Royal Sonesta Chicago Riverfront
Congress Plaza Hotel

Kid friendly vacation packages for 6-7 nights

Hyatt Regency McCormick Place
DoubleTree by Hilton Chicago - Magnificent Mile
Residence Inn Chicago Downtown/Loop

Kid friendly hotels in Chicago

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Book Chicago family vacations

Make your next family trip one for the books. When you choose family fun in Chicago, you’ll add some great shots to your photo album and make happy childhood memories for your little ones. Delight everyone in your group and make the most of your time together with family vacations to Chicago.

Find something for the whole family
Everyone in the family looks for something different on vacation. Kids need space to run and play, while teens are busy adding photo filters for social media. Mom and Dad just want to relax—and that can take many forms. When you book with Orbitz, we make sure you can relax in at least one way: You won’t have to worry about planning every detail of every day in Chicago. 

  • Easy planning: We have flights that fit your schedule and hotels that fit your family’s travel style. Bundle them together with our Chicago family vacation packages, and you save money and time—which can both be better spent on adventures.
  • Fun for everyone: You’ll never run out of things to do on family vacations in Chicago. Find kid-approved activities, parks and pools, and family-friendly restaurants. You could even find convenient amenities like laundry services and kitchenettes with apartment living.

Planning family vacations in Chicago should be fun. Don’t spend every waking hour comparing prices and amenities. When you book with Orbitz, we’ll make sure you get the best deal, so you can think about the important things, like ordering those matching family outfits. Chicago here you come!

How much does it cost to fly to Chicago?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Jun 26 - Sat, Jul 3
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$86
Spirit Airlines
Sat, Jul 31 - Mon, Aug 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$93
Spirit Airlines
Fri, Aug 20 - Fri, Aug 27
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$102
Frontier Airlines
Tue, Jun 22 - Tue, Jun 29
EWR
Liberty Intl.
ORD
O'Hare Intl.
$133
Spirit Airlines
Tue, Sep 14 - Tue, Sep 14
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$152
Delta
Fri, Sep 10 - Mon, Sep 13
EWR
Liberty Intl.
MDW
Midway Intl.
$162
Bargain Flight
Mon, Aug 16 - Tue, Aug 17
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$181
Bargain Flight
Thu, Mar 10 - Mon, Mar 14
GDL
Don Miguel Hidalgo y Costilla Intl.
ORD
O'Hare Intl.
$200
Volaris
Thu, Mar 24 - Mon, Mar 28
MEX
Mexico City Intl.
ORD
O'Hare Intl.
$203
Volaris
Thu, Mar 31 - Mon, Apr 4
GDL
Don Miguel Hidalgo y Costilla Intl.
MDW
Midway Intl.
$231
Volaris
Fri, Jun 18 - Sun, Jul 4
MEX
Mexico City Intl.
MDW
Midway Intl.
$350
Aeromexico