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.
3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
9.2/10 Wonderful! (303 reviews)
Jan 29 - Feb 1
3 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $428, price is now $247 per person
$247
per person
found 1 day ago
close to everything we will be staying here again on our next vacation to Chicago
Reviewed on Aug 31, 2024
4.5-star property
The Westin Michigan Avenue Chicago
Downtown Chicago
8.8/10 Excellent! (1,070 reviews)
Dec 10 - Dec 12
2 night stay
Boston (BOS) to Chicago (ORD)
Delta • Coach
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Coach
Price was $633, price is now $268 per person
$268
per person
found 19 hours ago
Everything is EXCELLENT. But don’t consider the hotel for breakfast lunch or dinner
Reviewed on Oct 18, 2025
4.5-star property
Pendry Chicago
Downtown Chicago
9.4/10 Exceptional! (1,110 reviews)
Jan 29 - Feb 1
3 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $546, price is now $307 per person
$307
per person
found 1 day ago
Pendry was historic and great
Reviewed on Jul 5, 2024
4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (367 reviews)
Jan 5 - Jan 9
4 night stay
Boston (BOS) to Chicago (ORD)
United • Coach
Chicago (ORD) to Boston (BOS)
JetBlue Airways • Coach
Save 100% on your flight
Price was $704, price is now $408 per person
$408
per person
found 17 hours ago
Front desk and maintenance staff was amazing super succeeded our expectations i will return gor future dates
Reviewed on Feb 16, 2024
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,761 reviews)
Jan 29 - Feb 1
3 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $812, price is now $477 per person
$477
per person
found 1 day ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!
Reviewed on Oct 13, 2025
Top rated hotels for your Central 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
0.76 mi from city center
$118 nightly
The price is $139 total per night
$139 total
Nov 23 - Nov 24
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
0.48 mi from city center
$116 nightly
The price is $136 total per night
$136 total
Nov 24 - Nov 25
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 securing valuables. Additional amenities include conference space, a business center, and express check-out.
Free WiFi
Restaurant
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
$101 nightly
The price is $119 total per night
$119 total
Nov 17 - Nov 18
Total with taxes and fees
Guests of Hilton Chicago/Magnificent Mile Suites enjoy a gym, free WiFi in public areas, and conference space. Valet parking is available for USD 82 per night. The front desk has multilingual staff on hand 24/7 to help with concierge services, luggage storage, and dry cleaning/laundry. Additional amenities include a business center, express check-out, and an ATM.
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.
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