Chicago Vacation Packages
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4.0-star property
Level Chicago - River North
Downtown Chicago
9.2/10 Wonderful! (1,120 reviews)
Nov 30 - Dec 3
3 night stay
Denver (DEN) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Denver (DEN)
Frontier Airlines • Coach
Save 100% on your flight
Price was $937, price is now $641 per person
$641
per person
found 1 day ago
Good location and parking, but the room has poor soundproofing, we can here the noise from outside
Reviewed on Oct 2, 2026
4.5-star property
Pendry Chicago
Downtown Chicago
9.2/10 Wonderful! (1,156 reviews)
Nov 12 - Nov 15
3 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,058, price is now $706 per person
$706
per person
found 1 day ago
Fantastic as always. Highly recommend
Reviewed on Oct 1, 2026
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.6/10 Exceptional! (2,035 reviews)
Dec 23 - Dec 27
4 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Contour Airlines • Coach
Save 100% on your flight
Price was $1,533, price is now $1,048 per person
$1,048
per person
found 1 day ago
5.0-star property
The Langham, Chicago
Downtown Chicago
9.8/10 Exceptional! (1,005 reviews)
Dec 23 - Dec 27
4 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Contour Airlines • Coach
Save 100% on your flight
Price was $1,593, price is now $1,106 per person
$1,106
per person
found 1 day ago
Our room was exceptionally clean with all the amenities. And we were especially impressed by the staff - everyone was friendly and anxious to help. A most enjoyable stay. We look forward to the next!
46676
Reviewed on Oct 3, 2026
4.0-star property
The Emily Hotel
Downtown Chicago
9.2/10 Wonderful! (1,346 reviews)
Nov 30 - Dec 3
3 night stay
Denver (DEN) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Denver (DEN)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,040, price is now $724 per person
$724
per person
found 1 day ago
Clean, easy to get to and walkable to the Fulton District. Great coffee shop.
Reviewed on Oct 2, 2026
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
$113 nightly
The price is $135 total per night
$135 total
Nov 2 - Nov 3
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 concierge services, luggage storage, and securing valuables. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
River Hotel
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.5 mi from city center
$167 nightly
The price is $199 total per night
$199 total
Nov 1 - Nov 2
Total with taxes and fees
River Hotel features a gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 76 per night. The front desk is staffed 24/7 to help with luggage storage, securing valuables, and concierge services. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include conference space, a business center, and express check-in.
Pet friendly
Free WiFi
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.74 mi from city center
$143 nightly
The price is $170 total per night
$170 total
Nov 1 - Nov 2
Total with taxes and fees
Guests of The Chicago Hotel Collection Ambassador Gold Coast enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 82 per night. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Additional amenities include conference space, express check-out, 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.
Things to do
Chicago CityPASS®: Experience 5 must-see attractions
$144
per adult
94% of travellers recommend
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