Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
3.0-star property
Aloft Bolingbrook
16.8/10 Exceptional! (1,005 reviews)
Jan 6 - Jan 11
5 night stay
Dallas (DFW) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Dallas (DFW)
American Airlines • Coach
Save 100% on your flight
Price was $431, price is now $259 per person
$259
per person
found 24 hours ago
Only complaint my shower water was not hot
Reviewed on Jul 2, 2025
4.5-star property
The Westin Michigan Avenue Chicago
Downtown Chicago
17.6/10 Exceptional! (1,075 reviews)
Dec 26 - Dec 31
5 night stay
Austin (AUS) to Chicago (ORD)
Frontier Airlines • Coach
Chicago (ORD) to Austin (AUS)
Spirit Airlines • Coach
Price was $1,446, price is now $527 per person
$527
per person
found 7 hours ago
Everything is EXCELLENT. But don’t consider the hotel for breakfast lunch or dinner
Reviewed on Oct 18, 2025
4.0-star property
The Emily Hotel
Downtown Chicago
18.4/10 Exceptional! (1,264 reviews)
Dec 27 - Jan 3
7 night stay
Austin (AUS) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,791, price is now $984 per person
$984
per person
found 1 day ago
Cute and trendy hotwl but there was a loud party on-site which ruined experience. It felt clean but our mini fridge had takeout left from former guest, so maid service obviously missed that.
Reviewed on Jul 26, 2025
4.0-star property
Level Chicago – Old Town
Downtown Chicago
18/10 Exceptional! (380 reviews)
Dec 27 - Jan 3
7 night stay
Austin (AUS) to Chicago (ORD)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,601, price is now $885 per person
$885
per person
found 1 day ago
We always love staying here. Such great service and nice accommodations.
Reviewed on Nov 20, 2025
4.0-star property
Arlo Chicago
Downtown Chicago
18.4/10 Exceptional! (1,862 reviews)
Jan 14 - Jan 18
4 night stay
Austin (AUS) to Chicago (ORD)
American Airlines • Non-stop • Coach
Chicago (ORD) to Austin (AUS)
Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $598, price is now $353 per person
$353
per person
found 1 day ago
Super convinient and great location.
Reviewed on Oct 25, 2025
Top rated hotels for your Chicago vacation package
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.05 mi from city center
The price is $145 total per night
$145 total
per night
Dec 21 - Dec 22
Guests of Palmer House a Hilton Hotel enjoy a full-service spa, an indoor pool, and a 24-hour gym. Parking is available for USD 57 per night (USD 85 per night for valet parking), and there's also limo/town car service. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, access to locker space, and luggage storage. Other amenities at this luxury hotel include a conference center, a business center, and express check-in.
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
The price is $102 total per night
$102 total
per night
Dec 21 - Dec 22
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 securing valuables, dry cleaning/laundry, and concierge services. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included
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 $134 total per night
$134 total
per night
Nov 26 - Nov 27
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.
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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