Central Chicago Vacation Packages
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Top Central Chicago vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Eurostars Magnificent Mile
Downtown Chicago
9/10 Wonderful! (3,314 reviews)
Jun 21 - Jun 23
2 night stay
Dallas (DFW) to Chicago (ORD)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $492, price is now $337 per person
$337
per person
found 2 days ago
In convenient area either by walking or uber
Reviewed on Oct 18, 2025
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (3,495 reviews)
Jun 25 - Jun 28
3 night stay
Dallas (DAL) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,078, price is now $601 per person
$601
per person
found 1 day ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.
Reviewed on Jan 14, 2026
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (453 reviews)
Jun 25 - Jun 28
3 night stay
Dallas (DFW) to Chicago (ORD)
Spirit Airlines • Coach
Chicago (ORD) to Dallas (DFW)
Frontier Airlines • Coach
Price was $1,203, price is now $780 per person
$780
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
Hotel Felix River North/Magnificent Mile
Downtown Chicago
8.2/10 Very Good! (2,582 reviews)
Jun 25 - Jun 28
3 night stay
Dallas (DAL) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $789, price is now $530 per person
$530
per person
found 1 day ago
The rooms were clean and smelled fresh.
Reviewed on Jan 8, 2026
4.5-star property
Pendry Chicago
Downtown Chicago
9.4/10 Exceptional! (1,140 reviews)
Jun 25 - Jun 28
3 night stay
Dallas (DAL) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,124, price is now $763 per person
$763
per person
found 1 day ago
Room was clean and comfortable. We really appreciated the chocolates and water!
Reviewed on Feb 25, 2026
Top rated hotels for your Central Chicago vacation package
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.27 mi from city center
$119 nightly
The price is $140 total per night
$140 total
Apr 12 - Apr 13
Total with taxes and fees
At Hilton Chicago/Magnificent Mile Suites, guests enjoy features like an indoor pool, a gym, and free WiFi in public areas. Valet parking is available for USD 82 per night. The front desk has multilingual staff on hand 24/7 to help with dry cleaning/laundry, securing valuables, and luggage storage. Additional amenities include conference space, a business center, and express check-out.
Pool
Pet friendly
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.48 mi from city center
$110 nightly
The price is $129 total per night
$129 total
Apr 16 - Apr 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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.76 mi from city center
$135 nightly
The price is $159 total per night
$159 total
Apr 12 - Apr 13
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 dry cleaning/laundry, concierge services, and luggage storage. Additional amenities include meeting rooms, conference space, and a business center.
Pool
Breakfast included
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View all propertiesLowest 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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