Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Popular Family Vacation Packages in Chicago

2 to 5 Day Family Packages

Family Hotels in Chicago

Estimated price for 1 night/2 adults

Hyatt Place Chicago/Lombard/Oak Brook
Hyatt Place Chicago/Lombard/Oak Brook
3.0 out of 5.0 2340 South Fountain Square Drive, Lombard, IL
Free Cancellation
4.4/5 (138 reviews)

The breakfast was not good ... I think it should’ve been a variety of meat

Reviewed on Mar 20, 2019
Family FriendlyBreakfastFree Breakfast
Embassy Suites Chicago Downtown
Embassy Suites Chicago Downtown
4.0 out of 5.0 600 N State St, Chicago, IL
4.2/5 (172 reviews)

staff was excellent, property, room and areas of hotel very well maintained

Reviewed on May 6, 2019
Family FriendlyBreakfastFree Breakfast
Hyatt Regency Chicago
Hyatt Regency Chicago
4.0 out of 5.0 151 East Wacker Dr, Chicago, IL
Free Cancellation
4.2/5 (914 reviews)

Great location downtown. A little confusing with the different towers and entrances. Almost missed our Go Express pick-up

Reviewed on May 15, 2019
Family FriendlyFitness CenterSports
Embassy Suites Chicago Downtown Magnificent Mile
Embassy Suites Chicago Downtown Magnificent Mile
4.0 out of 5.0 511 North Columbus Drive, Chicago, IL
Free Cancellation
4.1/5 (407 reviews)

Great location. Morning complimentary breakfast was exceptional with a chef preparing eggs to order 5:30 complimentary cocktails and snacks was a big surprise. Would definitely stay there again on my next visit to Chicago!

Reviewed on May 16, 2019
Family FriendlyBreakfastFree Breakfast
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4.0 out of 5.0 17 E Monroe St, Chicago, IL
Free Cancellation
4.1/5 (894 reviews)

No complaints. Great location, friendly staff and the building has alot on character.

Reviewed on May 13, 2019
Family FriendlyHistoricalConcierge
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5.0 520 South Michigan Avenue, Chicago, IL
Free Cancellation
3.5/5 (176 reviews)

it is good, the location, the enviroment, the staffs

Reviewed on May 15, 2019
Family FriendlyConciergeRoomservice

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!

Recently Reviewed Family Hotels

Recently Booked Family Hotels

*Savings based on all package bookings with Flight + Hotel made on from January 1, 2018 to December 31, 2018 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.