Chicago Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
3.0-star property
Sonesta Chicago O'Hare Airport Rosemont
O'Hare
8.6/10 Excellent! (1,573 reviews)
Nov 13 - Nov 16
3 night stay
Dallas (DFW) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $407, price is now $296 per person
$296
per person
found 1 day ago
Great location and Amazing restaurant downstairs
Reviewed on Sep 21, 2025
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,716 reviews)
Oct 24 - Oct 26
2 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $950, price is now $687 per person
$687
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
5.0-star property
Park Hyatt Chicago
Downtown Chicago
9.6/10 Exceptional! (1,001 reviews)
Oct 24 - Oct 26
2 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,018, price is now $753 per person
$753
per person
found 1 day ago
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.
Reviewed on Sep 13, 2024
4.5-star property
Pendry Chicago
Downtown Chicago
9.4/10 Exceptional! (1,085 reviews)
Nov 6 - Nov 9
3 night stay
Dallas (DFW) to Chicago (ORD)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $686, price is now $508 per person
$508
per person
found 1 day ago
Pendry was historic and great
Reviewed on Jul 5, 2024
4.0-star property
The Emily Hotel
Downtown Chicago
9.2/10 Wonderful! (1,222 reviews)
Oct 27 - Oct 29
2 night stay
Dallas (DFW) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Southwest Airlines • Coach
Save 100% on your flight
Price was $665, price is now $501 per person
$501
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
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 $197 total per night
$197 total
per night
Sep 22 - Sep 23
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
Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
15.67 mi from city center
The price is $252 total per night
$252 total
per night
Oct 18 - Oct 19
Guests of Hilton Chicago O'Hare Airport enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is USD 77 per day if you plan to drive, or hop aboard the free airport shuttle (available on request). Multilingual staff at the front desk are standing by 24/7 to help with concierge services, securing valuables, and luggage storage. Additional amenities include a conference center, a business center, and a computer station.
Free airport shuttle
Pet friendly
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.75 mi from city center
The price is $218 total per night
$218 total
per night
Oct 2 - Oct 3
Guests staying at Hilton Garden Inn Chicago Downtown/Magnificent Mile enjoy an indoor pool, a gym, and free WiFi in public areas. The front desk has multilingual staff on hand 24/7 to help with securing valuables, luggage storage, and tours or tickets. Additional amenities include meeting rooms, express check-out, and a porter/bellhop.
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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