Chicago Vacation Packages
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4.0-star property
The Glen Club
9/10 Wonderful! (391 reviews)
Oct 22 - Oct 25
3 night stay
Denver (DEN) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $471, price is now $328 per person
$328
per person
found 1 day ago
Property was awesome. Staff was excellent will return next time I am in the area.
Reviewed on Aug 30, 2026
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9.2/10 Wonderful! (520 reviews)
Nov 28 - Dec 1
3 night stay
Denver (DEN) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Denver (DEN)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,006, price is now $657 per person
$657
per person
found 20 hours ago
3.0-star property
Chicago Lake Shore Hotel
Kenwood
7/10 Good! (1,004 reviews)
Nov 13 - Nov 17
4 night stay
Minneapolis (MSP) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Minneapolis (MSP)
American Airlines • Coach
Save 100% on your flight
Price was $555, price is now $372 per person
$372
per person
found 1 day ago
clean room and friendly staff
Reviewed on Sep 10, 2026
4.0-star property
The Emily Hotel
Downtown Chicago
9.2/10 Wonderful! (1,338 reviews)
Oct 28 - Nov 2
5 night stay
Denver (DEN) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,188, price is now $817 per person
$817
per person
found 1 day ago
I enjoyed my stay at the Emily. Staff were friendly throughout my stay. I love the brand used for shower gel and shampoo. The only thing I would change, is the location of the full body mirror. I need to be able to back up and see myself. The bed restricted that and the flare from the window made it difficult to look at myself in daylight. Other than that, I’d stay there again. My first time in Chicago (thanks to Kanye) and I’m thrilled that my research brought me to the Emily.
Reviewed on Sep 11, 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
The price is $193 total per night
$193 total
per night
Sep 27 - Sep 28
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
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
The price is $213 total per night
$213 total
per night
Oct 12 - Oct 13
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
The price is $180 total per night
$180 total
per night
Sep 13 - Sep 14
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
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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