Central Chicago Vacation Packages
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Top Central Chicago vacation package deals
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4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
8.2/10 Very Good! (2,854 reviews)
Sep 3 - Sep 6
3 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $964, price is now $629 per person
$629
per person
found 1 day ago
Small quiet rooms, but the location makes up for it.
Reviewed on Jul 28, 2026
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
9.4/10 Exceptional! (2,606 reviews)
Oct 9 - Oct 12
3 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,804, price is now $1,212 per person
$1,212
per person
found 1 day ago
They let us check in early which was wonderful! Staff were extremely friendly and the valet was more than kind when I forgot a few items in my car. The room was clean and beautiful 😍
Reviewed on Jul 28, 2026
4.5-star property
Pendry Chicago
Downtown Chicago
9.2/10 Wonderful! (1,150 reviews)
Sep 3 - Sep 6
3 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,225, price is now $838 per person
$838
per person
found 1 day ago
The property is one of the coolest places in Chicago. Conveniently located to the Magnificent Mile, Millennial Park, and the Theater District.
Reviewed on Jul 28, 2026
Top rated hotels for your Central Chicago vacation package
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.48 mi from city center
$174 nightly
The price is $207 total per night
$207 total
Aug 16 - Aug 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 dry cleaning/laundry, concierge services, and securing valuables. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Free Cancellation
Reserve now, pay when you stay
1.67 mi from city center
$157 nightly
The price is $187 total per night
$187 total
Aug 23 - Aug 24
Total with taxes and fees
Guests of The Chicago Hotel Collection Ambassador Gold Coast enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 75 per night. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. Additional amenities include conference space, express check-out, and a banquet hall.
Pet friendly
Free WiFi
Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.9 mi from city center
$215 nightly
The price is $256 total per night
$256 total
Aug 9 - Aug 10
Total with taxes and fees
Guests of Omni Chicago Hotel have access to a 24-hour gym, in-room fitness, and free WiFi in public areas. Valet parking is offered for USD 89.49 per night. The 24-hour front desk has staff standing by to help with concierge services, dry cleaning/laundry, and securing valuables. Other amenities at this luxury hotel include conference space, express check-out, and a porter/bellhop.
Pet friendly
Free WiFi
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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.
Things to do
Chicago CityPASS®: Experience 5 must-see attractions
$144
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