Chicago Vacation Packages
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5.0-star property
Park Hyatt Chicago
Downtown Chicago
9.6/10 Exceptional! (1,000 reviews)
Oct 24 - Oct 27
3 night stay
Dallas (DFW) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • Coach
Save 100% on your flight
per person
found 1 day 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! (2,270 reviews)
Oct 17 - Oct 21
4 night stay
Dallas (DAL) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 23 hours ago
Very convenient to the heart of Chicago!
Nice hotel!
Reviewed on Jul 24, 2025
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,679 reviews)
Oct 17 - Oct 21
4 night stay
Dallas (DAL) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 23 hours ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!
Reviewed on Jun 16, 2025
3.0-star property
Holiday Inn Chicago O'Hare Area by IHG
O'Hare
7.8/10 Good! (1,004 reviews)
Oct 9 - Oct 14
5 night stay
Dallas (DFW) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • Coach
Save 100% on your flight
per person
found 10 hours ago
Close to airport
Excellent!!
Reviewed on Nov 11, 2023
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 $184 total per night
$184 total
per night
Sep 1 - Sep 2
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 dry cleaning/laundry, concierge services, and securing valuables. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.05 mi from city center
The price is $229 total per night
$229 total
per night
Aug 22 - Aug 23
Guests of Palmer House a Hilton Hotel enjoy a full-service spa, an indoor pool, and a 24-hour gym. Parking is available for USD 57 per night (USD 85 per night for valet parking), and there's also limo/town car service. Multilingual staff at the front desk are standing by 24/7 to help with access to locker space, luggage storage, and dry cleaning/laundry. Other amenities at this luxury hotel include a conference center, a business center, and express check-in.
Pool
Spa
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
Free Cancellation
0.98 mi from city center
The price is $171 total per night
$171 total
per night
Aug 24 - Aug 25
Guests of Crowne Plaza Chicago West Loop by IHG enjoy a gym, free WiFi in public areas, and conference space. Self parking is offered for USD 54.00 per day. Multilingual staff at the 24-hour front desk can assist with securing valuables, dry cleaning/laundry, and luggage storage. Additional amenities include a 24-hour business center, express check-in, and express check-out.
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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