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
La Banque Hotel
9.4/10 Exceptional! (434 reviews)
Nov 12 - Nov 15
3 night stay
Los Angeles (LAX) to Chicago (ORD)
Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $597, price is now $365 per person
$365
per person
found 10 hours ago
Beautiful boutique hotel with great staff!
Reviewed on Sep 16, 2022
4.0-star property
The Emily Hotel
Downtown Chicago
9.2/10 Wonderful! (1,192 reviews)
Nov 11 - Nov 16
5 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Price was $1,466, price is now $748 per person
$748
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
4.5-star property
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
9/10 Wonderful! (1,002 reviews)
Nov 11 - Nov 16
5 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $913, price is now $537 per person
$537
per person
found 1 day ago
Rooms small but clean.
Reviewed on Aug 14, 2025
4.0-star property
Hilton Chicago O'Hare Airport
O'Hare
8.2/10 Very Good! (2,103 reviews)
Nov 11 - Nov 16
5 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,012, price is now $614 per person
$614
per person
found 1 day ago
Good place to stay when flights leave early the next morning.
Reviewed on Aug 21, 2025
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (2,342 reviews)
Oct 31 - Nov 2
2 night stay
Atlanta (ATL) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $782, price is now $477 per person
$477
per person
found 1 day ago
One day didn’t receive room service
Reviewed on Sep 2, 2025
Top rated hotels for your Chicago vacation package
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
$183 nightly
The price is $215 total per night
$215 total
Sep 22 - Sep 23
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 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
$179 nightly
The price is $210 total per night
$210 total
Sep 16 - Sep 17
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 dry cleaning/laundry. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
The Wade
644 N Lake Shore Dr, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
1.12 mi from city center
$167 nightly
The price is $196 total per night
$196 total
Sep 22 - Sep 23
Total with taxes and fees
At The Wade, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. Valet parking is offered for USD 86 per night. The 24-hour front desk has staff standing by to help with securing valuables, concierge services, and dry cleaning/laundry. Other amenities at this luxury hotel include conference space, a 24-hour business center, and express check-in.
Pool
Pet friendly
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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