Find Family Hotels in Westchester, IL

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Westchester Family Hotels

Tonight
6 Dec - 7 Dec
Tomorrow
7 Dec - 8 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Top Westchester Family Hotels

Breakfast and dinner served
Four Points by Sheraton Chicago Westchester/Oak Brook

Four Points by Sheraton Chicago Westchester/Oak Brook

3.0 star property
Westchester
8.6 out of 10, Excellent, (1004)
"Friendly staff and very clean rooms will book again"
United States
Curtrina
The price is SAR 379
SAR 424 total
includes taxes & fees
15 Dec - 16 Dec
Four Points by Sheraton Chicago Westchester/Oak Brook
Fridge, microwave, oven, stovetop
Modern 3BR Home w/ Huge Backyard | LCP Collection

Modern 3BR Home w/ Huge Backyard | LCP Collection

Westchester
10.0 out of 10, Exceptional, (1)
"Everything was exactly like we hoped and ghen sum. Great single level floor plan with garage access."
United States
Alva E.
Modern 3BR Home w/ Huge Backyard | LCP Collection
Premium Private Quad | Premium bedding, in-room safe, blackout drapes, iron/ironing board
Freehand Chicago

Freehand Chicago

4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (2621)
"Great location "
United States
Stacy
The price is SAR 236
SAR 343 total
includes taxes & fees
6 Jan - 7 January 2026
Freehand Chicago
Reception
Swissotel - Chicago

Swissotel - Chicago

4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2994)
"Great stay"
Canada
Lorrington Ashford
The price is SAR 428
SAR 612 total
includes taxes & fees
2 Jan - 3 January 2026
Swissotel - Chicago
Exterior
FOUND Hotel Chicago River North

FOUND Hotel Chicago River North

2.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (359)
"love this place definitely coming back !"
United States
Dayanara
The price is SAR 221
SAR 260 total
includes taxes & fees
5 Jan - 6 January 2026
FOUND Hotel Chicago River North
Lobby sitting area
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (2999)
"Enjoyed this hotel stay. "
United States
Kimberly
The price is SAR 315
SAR 480 total
includes taxes & fees
4 Jan - 5 January 2026
Warwick Allerton - Chicago
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3138)
"Amazing and will be staying again!"
United States
Angie
The price is SAR 324
SAR 381 total
includes taxes & fees
4 Jan - 5 January 2026
Eurostars Magnificent Mile
Junior Suite, 1 King Bed (Family) | Hypo-allergenic bedding, down comforters, pillowtop beds, in-room safe
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3112)
"nice room, great bfast at the bar"
United States
Jon Scott
The price is SAR 428
SAR 622 total
includes taxes & fees
3 Jan - 4 January 2026
The Royal Sonesta Chicago Downtown
Cocktail bar
Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1476)
"Loved this hotel, great location, pet friendly."
United States
Tracy
The price is SAR 259
SAR 414 total
includes taxes & fees
4 Jan - 5 January 2026
Claridge House Chicago, Tapestry Collection by Hilton
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (2117)
"Loved and enjoyed our stay"
United States
Luis
The price is SAR 385
SAR 545 total
includes taxes & fees
28 Dec - 29 Dec
Palmer House a Hilton Hotel
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.
View all properties

Top Westchester Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Thank to Mr.Robert for getting a good room with a beautiful view of the river "
Armando 4-night trip
Posted 4 hours ago
The Royal Sonesta Chicago Downtown

Explore a world of travel with Expedia

Frequently asked questions

What's Westchester like for family-friendly vacations?
You might want to consider the welcoming destination of Westchester if you've been thinking about a trip for the whole family. The basketball games, golfing, and restaurants are just some of the things that make this an attractive family vacation spot. Arrange a flight into Chicago Midway Airport (MDW), which is the closest airport, or Chicago O'Hare Intl. Airport (ORD), which is located 8.9 mi (14.3 km) from the city center.
When's the best time to book a family-friendly vacation in Westchester?
The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Westchester are January, November, February, and December, with each month seeing an average of 5 inches of snowfall.
What's there to see and do with your family in Westchester?
While you and your family are visiting Westchester, you might want to check out some kid-friendly attractions such as Wrigley Field, Michigan Avenue, and United Center. Make sure you have plenty of time to take in activities in the area like Soldier Field and Navy Pier.