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
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (2,373 reviews)
Oct 15 - Oct 17
2 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Coach
Chicago (ORD) to Boston (BOS)
United • Coach
Save 100% on your flight
Price was $837, price is now $474 per person
$474
per person
found 1 day ago
One day didn’t receive room service
Reviewed on Sep 2, 2025
4.0-star property
Palmer House a Hilton Hotel
Downtown Chicago
8.4/10 Very Good! (1,917 reviews)
Nov 1 - Nov 9
8 night stay
Boston (BOS) to Chicago (ORD)
Delta • Coach
Chicago (ORD) to Boston (BOS)
United • Coach
Save 100% on your flight
Price was $1,495, price is now $865 per person
$865
per person
found 1 day ago
Loved the Palmer House Hotel!!! The lobby, amazing decoration! I even took a picture of it to post on social. The bar and restaurant area, very popular and looked like everyone was enjoying themselves! The room, well, not the best, but this was an occasion where I booked last minute and through a 3rd party on lalapalooza weekend. So, I was happy to just get a bed and a shower! But could use some upgrades. Overall, the help was extremely courteous and helpful. The amenities were perfectly accommodating and it gave me and my daughter a place to comfortably call home for the night! I would recommend this hotel to anyone!
Reviewed on Aug 15, 2025
4.5-star property
Thompson Chicago, by Hyatt
Downtown Chicago
9.2/10 Wonderful! (1,224 reviews)
Nov 1 - Nov 9
8 night stay
Boston (BOS) to Chicago (ORD)
Delta • Coach
Chicago (ORD) to Boston (BOS)
United • Coach
Save 100% on your flight
Price was $1,575, price is now $1,052 per person
$1,052
per person
found 1 day ago
This was my first time in Chicago, and I had an incredible time. I highly recommend staying at this hotel.
Reviewed on Aug 22, 2025
4.0-star property
Silversmith Hotel Chicago Downtown
Downtown Chicago
9.4/10 Exceptional! (1,965 reviews)
Nov 1 - Nov 9
8 night stay
Boston (BOS) to Chicago (ORD)
Delta • Coach
Chicago (ORD) to Boston (BOS)
United • Coach
Save 100% on your flight
Price was $1,059, price is now $726 per person
$726
per person
found 1 day ago
This was my second time staying at Silversmith. Love the location of the hotel. I wish I remember the name of the woman who checked us in but the whole staff is fantastic. I have had nothing but good experiences when staying here. Will be my go to hotel for Chicago.
Reviewed on Sep 9, 2025
3.0-star property
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
8.8/10 Excellent! (1,653 reviews)
Nov 1 - Nov 9
8 night stay
Boston (BOS) to Chicago (ORD)
Delta • Coach
Chicago (ORD) to Boston (BOS)
United • Coach
Save 100% on your flight
Price was $1,301, price is now $911 per person
$911
per person
found 1 day ago
The location was good
Reviewed on Aug 6, 2025
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
$179 nightly
The price is $210 total per night
$210 total
Sep 22 - Sep 23
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
$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
Freehand Chicago
19 East Ohio Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.74 mi from city center
$137 nightly
The price is $160 total per night
$160 total
Sep 23 - Sep 24
Total with taxes and fees
Guests of Freehand Chicago enjoy features like a 24-hour gym, free WiFi in public areas, and express check-in. Self parking is offered for USD 49 per night. Multilingual staff at the 24-hour front desk can assist with luggage storage, tours or tickets, and dry cleaning/laundry. Additional amenities include express check-out, laundry facilities, and a water dispenser.
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.
