Chicago Vacation Packages
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Top Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
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
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (5,174 reviews)
Nov 5 - Nov 9
4 night stay
Nashville (BNA) to Chicago (ORD)
Contour Airlines • Non-stop • Coach
Chicago (ORD) to Nashville (BNA)
Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,283, price is now $794 per person
$794
per person
found 1 day ago
Nice Stay wifi was ok really not working well once you step out of the hotel better control
Reviewed on Sep 11, 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 18 hours ago
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
9.2/10 Wonderful! (561 reviews)
Oct 17 - Oct 21
4 night stay
Nashville (BNA) to Chicago (ORD)
American Airlines • FirstClass
Chicago (ORD) to Nashville (BNA)
Frontier Airlines • FirstClass
Save 100% on your flight
Price was $1,966, price is now $1,342 per person
$1,342
per person
found 1 day ago
4.0-star property
The Emily Hotel
Downtown Chicago
9.2/10 Wonderful! (1,338 reviews)
Oct 17 - Oct 21
4 night stay
Nashville (BNA) to Chicago (ORD)
American Airlines • FirstClass
Chicago (ORD) to Nashville (BNA)
Frontier Airlines • FirstClass
Save 100% on your flight
Price was $2,253, price is now $1,545 per person
$1,545
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
$162 nightly
The price is $193 total per night
$193 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.
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
$179 nightly
The price is $213 total per night
$213 total
Oct 12 - Oct 13
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
$151 nightly
The price is $180 total per night
$180 total
Sep 13 - Sep 14
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
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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