Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.5-star property
The Royal Sonesta Chicago River North
Downtown Chicago
9.2/10 Wonderful! (1,950 reviews)
Oct 5 - Oct 10
5 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
We received liked the service the staff provided, particularly Shanda.
Reviewed on Jul 20, 2025
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,659 reviews)
Oct 5 - Oct 10
5 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
per person
found 1 day ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!
Reviewed on Jun 16, 2025
4.0-star property
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
8.8/10 Excellent! (1,922 reviews)
Oct 5 - Oct 10
5 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Attitude of the people was outstanding!! Very friendly and helpful.
Reviewed on Jun 13, 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
$157 nightly
The price is $184 total per night
$184 total
Sep 1 - Sep 2
Total includes 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 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
$198 nightly
The price is $229 total per night
$229 total
Aug 21 - Aug 22
Total includes taxes and fees
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, concierge services, and dry cleaning/laundry. Other amenities at this spa 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
$146 nightly
The price is $171 total per night
$171 total
Aug 24 - Aug 25
Total includes taxes and fees
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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