Chicago Vacation Packages
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4.0-star property
Level Chicago - River North
Downtown Chicago
9/10 Wonderful! (721 reviews)
Jan 8 - Jan 12
4 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $563, price is now $324 per person
$324
per person
found 1 day ago
The pool area is fantastic. Rooms very ample-sized and comfortable. I would stay here again!
Reviewed on Jul 8, 2024
4.5-star property
The Westin Michigan Avenue Chicago
Downtown Chicago
8.8/10 Excellent! (1,070 reviews)
Dec 27 - Dec 31
4 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Price was $1,127, price is now $462 per person
$462
per person
found 1 day ago
Everything is EXCELLENT. But don’t consider the hotel for breakfast lunch or dinner
Reviewed on Oct 18, 2025
5.0-star property
Park Hyatt Chicago
Downtown Chicago
9.6/10 Exceptional! (1,006 reviews)
Dec 26 - Dec 29
3 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $993, price is now $610 per person
$610
per person
found 15 hours ago
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.
Reviewed on Sep 13, 2024
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (2,602 reviews)
Nov 22 - Nov 24
2 night stay
Boston (BOS) to Chicago (ORD)
Delta • Coach
Chicago (ORD) to Boston (BOS)
United • Coach
Save 100% on your flight
Price was $549, price is now $345 per person
$345
per person
found 1 day ago
One day didn’t receive room service
Reviewed on Sep 2, 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
The price is $170 total per night
$170 total
per night
Nov 2 - Nov 3
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 concierge services, luggage storage, and securing valuables. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
1.35 mi from city center
The price is $129 total per night
$129 total
per night
Nov 16 - Nov 17
Guests of Hilton Chicago/Magnificent Mile Suites enjoy a gym, free WiFi in public areas, and conference space. Valet parking is available for USD 82 per night. The front desk has multilingual staff on hand 24/7 to help with securing valuables, dry cleaning/laundry, and luggage storage. Additional amenities include a business center, express check-out, and a porter/bellhop.
Pet friendly
Free WiFi
Freehand Chicago
19 East Ohio Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.81 mi from city center
The price is $112 total per night
$112 total
per night
Nov 10 - Nov 11
Guests of Freehand Chicago enjoy features like a 24-hour gym, free WiFi in public areas, and express check-in. Self parking is offered for USD 49 per night. Multilingual staff at the 24-hour front desk can assist with tours or tickets, dry cleaning/laundry, and luggage storage. Additional amenities include express check-out, laundry facilities, and a fireplace in the lobby.
Pet friendly
Free WiFi
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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