Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (561 reviews)
Nov 27 - Dec 1
4 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 $978, price is now $696 per person
$696
per person
found 1 day ago
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9.2/10 Wonderful! (520 reviews)
Nov 27 - Dec 1
4 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 $1,232, price is now $759 per person
$759
per person
found 1 day ago
4.5-star property
Swissotel - Chicago
Downtown Chicago
9/10 Wonderful! (3,512 reviews)
Oct 21 - Oct 24
3 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,431, price is now $940 per person
$940
per person
found 1 day ago
The hotel was very good and in a great location. The only thing I would have asked to improve is the breakfast selection which was very basic and limited.
Reviewed on Sep 13, 2026
4.0-star property
Stay One Chicago
Downtown Chicago
7.8/10 Good! (12 reviews)
Nov 27 - Dec 1
4 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 $1,495, price is now $994 per person
$994
per person
found 1 day ago
Top rated hotels for your Chicago vacation package
River Hotel
75 East Wacker Drive Chicago IL
0.5 mi from city center
$152 nightly
The price is $181 total per night
$181 total
Sep 27 - Sep 28
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.
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
$179 nightly
The price is $213 total per night
$213 total
Oct 13 - Oct 14
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
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
$164 nightly
The price is $195 total per night
$195 total
Sep 27 - Sep 28
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.
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: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
Chicago CityPASS®: Experience 5 must-see attractions
$144
per adult
94% of travellers recommend
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