Chicago Vacation Packages
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Top Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
8.8/10 Excellent! (2,269 reviews)
Aug 11 - Aug 15
4 night stay
Atlanta (ATL) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Great spot, great room! Offered us a free upgrade!
Reviewed on May 19, 2025
4.0-star property
Palmer House a Hilton Hotel
Downtown Chicago
8.4/10 Very Good! (1,733 reviews)
Aug 11 - Aug 15
4 night stay
Atlanta (ATL) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Amazing hotel. My wife and I love staying here.
Reviewed on May 28, 2025
2.5-star property
Hampton Inn Chicago/Naperville
9/10 Wonderful! (1,000 reviews)
Aug 3 - Aug 8
5 night stay
Dallas (DFW) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 5 hours ago
It is fine, but I find most Hampton Inns to be a little bit better.
Reviewed on Aug 4, 2024
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,598 reviews)
Aug 11 - Aug 15
4 night stay
Atlanta (ATL) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Perfect stay. Great hotel. Only complaint is the death spot in the bedroom. Gross looking stain on the floor: other than that- perfect.
Reviewed on Jun 1, 2025
4.0-star property
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
8.4/10 Very Good! (4,131 reviews)
Aug 11 - Aug 15
4 night stay
Atlanta (ATL) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Great location, many good restaurants around.
Reviewed on May 27, 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
$127 nightly
The price is $150 total per night
$150 total
Jul 1 - Jul 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, securing valuables, and concierge services. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.46 mi from city center
$144 nightly
The price is $169 total per night
$169 total
Jul 1 - Jul 2
Total includes taxes and fees
At citizenM Chicago Downtown, guests have access to a gym, free WiFi in public areas, and a 24-hour business center. The 24-hour front desk has staff standing by to help with luggage storage and securing valuables. Additional amenities include coffee/tea in a common area, a computer station, and express check-in.
Free WiFi
Restaurant
The Westin Michigan Avenue Chicago
909 North Michigan Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
1.29 mi from city center
$169 nightly
The price is $198 total per night
$198 total
Jun 30 - Jul 1
Total includes taxes and fees
Guests staying at The Westin Michigan Avenue Chicago enjoy access to a full-service spa, a 24-hour gym, and free WiFi in public areas. Valet parking is available for USD 79 per day. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, securing valuables, and concierge services. Other amenities at this luxury hotel include conference space, a 24-hour business center, and coffee/tea in a common area.
Spa
Pet friendly
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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