Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (2,427 reviews)
Dec 25 - Dec 29
4 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Boston (BOS)
Southwest Airlines • Coach
Save 100% on your flight
Price was $745, price is now $439 per person
$439
per person
found 1 day ago
One day didn’t receive room service
Reviewed on Sep 2, 2025
4.5-star property
The Westin Michigan Avenue Chicago
Downtown Chicago
8.8/10 Excellent! (1,046 reviews)
Dec 23 - Dec 28
5 night stay
Boston (BOS) to Chicago (ORD)
United • Coach
Chicago (ORD) to Boston (BOS)
Southwest Airlines • Coach
Price was $1,614, price is now $669 per person
$669
per person
found 1 day ago
Great hotel. Would be nice to have a map of first floor dining options and hours open.
Reviewed on Sep 7, 2025
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,716 reviews)
Dec 25 - Dec 29
4 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Boston (BOS)
Southwest Airlines • Coach
Save 100% on your flight
Price was $1,423, price is now $845 per person
$845
per person
found 1 day ago
Every employee makes every guest feel like a rockstar. Commitment to quality and guest experience is evident.
Reviewed on Sep 14, 2025
4.5-star property
Pendry Chicago
Downtown Chicago
9.4/10 Exceptional! (1,085 reviews)
Dec 25 - Dec 29
4 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Coach
Chicago (ORD) to Boston (BOS)
Southwest Airlines • Coach
Save 100% on your flight
Price was $769, price is now $472 per person
$472
per person
found 1 day ago
Pendry was historic and great
Reviewed on Jul 5, 2024
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
$145 nightly
The price is $170 total per night
$170 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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.83 mi from city center
$152 nightly
The price is $179 total per night
$179 total
Nov 9 - Nov 10
Total with taxes and fees
Guests of Embassy Suites by Hilton Chicago Downtown River North have access to an indoor pool, a gym, and WiFi in public areas. Valet parking is available for USD 79.00 per night. Multilingual staff at the front desk are standing by 24/7 to help with concierge services, securing valuables, and luggage storage. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included
Freehand Chicago
19 East Ohio Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.81 mi from city center
$95 nightly
The price is $112 total per night
$112 total
Nov 10 - Nov 11
Total with taxes and fees
Guests of Freehand Chicago enjoy features like a 24-hour gym, free WiFi in public areas, and express check-in. Self parking is offered for USD 49 per night. Multilingual staff at the 24-hour front desk can assist with tours or tickets, dry cleaning/laundry, and luggage storage. Additional amenities include express check-out, laundry facilities, 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.
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