Find kid-friendly hotels & resorts in Oakland, Chicago from $77

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Check availability on Oakland Family Hotels

Our top choices for Oakland family-friendly hotels

Premium Private Quad | Premium bedding, in-room safe, blackout drapes, iron/ironing board
Freehand Chicago

Freehand Chicago

Freehand Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very Good, (2638)
"The room was spotless and the staff where great!"
United States
Maria
$65 nightly
The price is $77
Jan 4 - Jan 5, 2026
Total with taxes and fees
Freehand Chicago
Reception
River Hotel

River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (4847)
"Great location, comfortable room, and nice staff."
United States
Claudia
$88 nightly
The price is $103
Dec 18 - Dec 19
Total with taxes and fees
River Hotel
Lobby sitting area
Warwick Allerton - Chicago

Warwick Allerton - Chicago

Warwick Allerton - Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (3006)
"Enjoyed this hotel stay. "
United States
Kimberly
$88 nightly
The price is $104
Dec 21 - Dec 22
Total with taxes and fees
Warwick Allerton - Chicago
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2258)
"This place was amazing !"
United States
Jayla Danyell
$122 nightly
The price is $143
Jan 6 - Jan 7, 2026
Total with taxes and fees
Sable at Navy Pier Chicago, Curio Collection by Hilton
Exterior
Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (2739)
"Great food clean room friendly staff"
United States
MARINA
$98 nightly
The price is $115
Dec 23 - Dec 24
Total with taxes and fees
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Reception
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3144)
"Great location "
United States
Christian
$86 nightly
The price is $101
Jan 11 - Jan 12, 2026
Total with taxes and fees
Eurostars Magnificent Mile
Ballroom
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (2124)
"Loved and enjoyed our stay"
United States
Luis
$136 nightly
The price is $155
Dec 21 - Dec 22
Total with taxes and fees
Palmer House a Hilton Hotel
Pool
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1754)
"Clean and staff was courteous. "
United States
HANNAH
$71 nightly
The price is $84
Jan 5 - Jan 6, 2026
Total with taxes and fees
Hilton Garden Inn Chicago Downtown South Loop
Cocktail bar
Claridge House Chicago, Tapestry Collection by Hilton

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, (1478)
"I really liked this location - we will stay here again. "
United States
Lynnsey
$94 nightly
The price is $110
Dec 21 - Dec 22
Total with taxes and fees
Claridge House Chicago, Tapestry Collection by Hilton
Breakfast, lunch and dinner served
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (3302)
"Great location!"
Mexico
Jose
$87 nightly
The price is $102
Dec 18 - Dec 19
Total with taxes and fees
Club Quarters Hotel, Central Loop, Chicago
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.
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Top Oakland Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Excelleny"
Kimberly 1-night trip
Posted 9 hours ago
Hyatt Regency Chicago

Frequently asked questions

What's Oakland like for family-friendly vacations?
The destination of Oakland is a great choice if you've been thinking about a vacation with your kids. The beaches, lake views, and soaring skyscrapers are just a few things that make this an attractive place for families. Fly into Chicago Midway Airport (MDW), which is the closest airport, or Chicago O'Hare Intl. Airport (ORD), which is located 18.8 mi (30.3 km) from the center of Oakland.
What's there to see and do with your family in Oakland?
Michigan Avenue and Wrigley Field are interesting attractions you and your family might enjoy exploring while you are staying in Oakland. Make sure you have plenty of time to take in activities in the area like Soldier Field, Navy Pier, and United Center.

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