Chicago Vacation Packages
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4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
8.2/10 Very Good! (2,779 reviews)
Aug 21 - Aug 24
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $785, price is now $511 per person
$511
per person
found 1 day ago
Best vibe. In the mix!
Reviewed on May 2, 2026
3.0-star property
Great Wolf Lodge Illinois
8.6/10 Excellent! (1,003 reviews)
Aug 21 - Aug 24
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,067, price is now $549 per person
$549
per person
found 1 day ago
Clean rooms. Waterpark area and hallways are well maintained. Convenient dining options inside the lodge as well as close by
Reviewed on Nov 23, 2023
2.5-star property
Hampton Inn & Suites Chicago Medical District UIC
Near West Side
9.6/10 Exceptional! (622 reviews)
Aug 23 - Aug 28
5 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,070, price is now $664 per person
$664
per person
found 1 day ago
We stayed one night and attended the sweet sixteen game at the United Center. The hotel was very easy to get to and park at. We were pleasantly surprised by the cleanliness of all areas. Our room was huge and had everything we needed. The free breakfast had a lot of options and was good.
Reviewed on Mar 28, 2026
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (4,391 reviews)
Aug 21 - Aug 24
3 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,078, price is now $683 per person
$683
per person
found 1 day ago
The room was comfortable and clean. The lobby could stand a refresh.
Reviewed on Jun 19, 2026
3.5-star property
The Chicago Hotel Collection - Wrigleyville
Lakeview
7/10 Good! (1,023 reviews)
Aug 23 - Aug 28
5 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,247, price is now $794 per person
$794
per person
found 1 day ago
Staff was great, very helpful.
Reviewed on Nov 18, 2025
Top rated hotels for your Chicago vacation package
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
$136 nightly
The price is $162 total per night
$162 total
Jun 29 - Jun 30
Total with taxes and fees
Guests of Congress Plaza Hotel enjoy a gym, free WiFi in public areas, and meeting rooms. Self parking is offered for USD 62.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, concierge services, and luggage storage. Additional amenities include conference space, a business center, and express check-out.
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Free Cancellation
Reserve now, pay when you stay
13.75 mi from city center
$135 nightly
The price is $154 total per night
$154 total
Jun 28 - Jun 29
Total with taxes and fees
At Hyatt Regency O'Hare Chicago, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. If you drive, self parking is USD 45 per night, or you can take advantage of the free airport shuttle (available 24 hours). Multilingual staff at the front desk are standing by 24/7 to help with luggage storage, securing valuables, and tours or tickets. Additional amenities include conference space, a business center, and a microwave in a common area.
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Free Cancellation
1.07 mi from city center
$131 nightly
The price is $155 total per night
$155 total
Jun 29 - Jun 30
Total with taxes and fees
Guests of The Chicago Hotel Collection - Magnificent Mile enjoy features like a 24-hour gym, free WiFi in public areas, and express check-out. Self parking is available for USD 58 per night. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Other amenities at this boutique hotel include a TV in a common area, wedding services, and a reception hall.
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.
Things to do
Chicago CityPASS®: Experience 5 must-see attractions
$144
per adult
94% of travellers recommend
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