Central Chicago Vacation Packages

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Kinzie Hotel
4.0-star property

Kinzie Hotel

Downtown Chicago
9.2/10 Wonderful! (1,993 reviews)

Mar 26 - Mar 31

5 night stay

Boston (BOS) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $669, price is now $453 per person
$453
per person
found 1 day ago
Nice hotel in the heart of downtown; many good restaurants plus the Grand Red Line "L" Station within walking distance. Toilet clogged up unfortunately.

Reviewed on Nov 28, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
9.4/10 Exceptional! (2,229 reviews)

Mar 26 - Mar 31

5 night stay

Boston (BOS) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $734, price is now $500 per person
$500
per person
found 1 day ago
Courteous staff, clean room, conveniently located right on the pier.

Reviewed on Nov 3, 2025

Viceroy Chicago
4.5-star property

Viceroy Chicago

Downtown Chicago
9.4/10 Exceptional! (1,129 reviews)

Mar 26 - Mar 31

5 night stay

Boston (BOS) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $991, price is now $677 per person
$677
per person
found 1 day ago
Fantastic Aria for shopping and dining. The beach is close, too. The only negative I can say is we try to valet our car and there were two cars in front of the hotel and we could not even pull up behind them. We had to drive to the closest parking garage and park and we’ll our luggage to the hotel. Other than that, it was a perfect day!

Reviewed on Sep 23, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Downtown Chicago
9.4/10 Exceptional! (2,790 reviews)

Apr 17 - Apr 19

2 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Price was $666, price is now $487 per person
$487
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

Hilton Grand Vacations Club Chicago Magnificent Mile
3.5-star property

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago
9.2/10 Wonderful! (317 reviews)

Mar 26 - Mar 31

5 night stay

Boston (BOS) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $745, price is now $546 per person
$546
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

Top rated hotels for your Central Chicago vacation package

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.48 mi from city center
$93 nightly
The price is $109 total per night
$109 total
Feb 16 - Feb 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.84 mi from city center
$143 nightly
The price is $167 total per night
$167 total
Mar 4 - Mar 5
Total with taxes and fees
A 24-hour gym and free WiFi in public areas are features at Hotel Riu Plaza Chicago. Multilingual staff at the 24-hour front desk can assist with luggage storage, concierge services, and dry cleaning/laundry.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.76 mi from city center
$103 nightly
The price is $120 total per night
$120 total
Feb 22 - Feb 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 luggage storage. Additional amenities include meeting rooms, conference space, and a business center.
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