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
The Buckingham Hotel
Downtown Chicago
9/10 Wonderful! (1,007 reviews)
Jan 22 - Jan 26
4 night stay
Houston (IAH) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Price was $684, price is now $492 per person
$492
per person
found 1 day ago
beautiful view gorgeous room
Reviewed on Oct 26, 2026
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (5,555 reviews)
Dec 3 - Dec 7
4 night stay
Boston (BOS) to Chicago (ORD)
JetBlue Airways • Roundtrip • Coach
Price was $1,253, price is now $785 per person
$785
per person
found 1 day ago
The Riu in Chicago was in a great location downtown. The rooftop bar offered great views, drinks and food. The breakfast buffet was one of the best we've ever had. The room was clean and quiet. You can't ask for more!
Reviewed on Oct 28, 2026
5.0-star property
The Peninsula Chicago
Downtown Chicago
9.8/10 Exceptional! (1,000 reviews)
Jan 11 - Jan 15
4 night stay
Houston (IAH) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Houston (IAH)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,502, price is now $963 per person
$963
per person
found 1 day ago
4.0-star property
Stay One Chicago
Downtown Chicago
8.4/10 Very Good! (21 reviews)
Jan 9 - Jan 12
3 night stay
Houston (IAH) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Price was $890, price is now $640 per person
$640
per person
found 16 hours ago
A must stay, views from the unit was amazing. Will stay here again. The only issue was the Door lock app. It kept removing the elevator from the list so I had to contact customer service a few times. Other than that our stay was amazing.
Reviewed on Oct 22, 2026
4.0-star property
Level Chicago - River North
Downtown Chicago
9.2/10 Wonderful! (1,149 reviews)
Nov 27 - Dec 2
5 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Coach
Save 100% on your flight
Price was $1,467, price is now $1,104 per person
$1,104
per person
found 1 day ago
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
$106 nightly
The price is $126 total per night
$126 total
Nov 25 - Nov 26
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 securing valuables, concierge services, and dry cleaning/laundry. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
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
$116 nightly
The price is $138 total per night
$138 total
Oct 29 - Oct 30
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
River Hotel
75 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.5 mi from city center
$116 nightly
The price is $138 total per night
$138 total
Nov 22 - Nov 23
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 securing valuables, concierge services, and dry cleaning/laundry. 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
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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