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4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
8.2/10 Very Good! (2,744 reviews)
Sep 3 - Sep 7
4 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,027, price is now $621 per person
$621
per person
found 1 day ago
Best vibe. In the mix!
Reviewed on May 2, 2026

4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (4,319 reviews)
Sep 3 - Sep 7
4 night stay
Boston (BOS) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,313, price is now $780 per person
$780
per person
found 1 day ago
Nice staff. Clean. Great rooftop bar!! Great location. Great included breakfast buffet!
I prefer a comforter rather than a sheet and blanket but still loved it!!
Reviewed on Jun 5, 2026

4.0-star property
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
8.4/10 Very Good! (1,954 reviews)
Jul 15 - Jul 19
4 night stay
Boston (BOS) to Chicago (ORD)
Delta • Coach
Chicago (ORD) to Boston (BOS)
Southwest Airlines • Coach
Save 100% on your flight
Price was $1,100, price is now $665 per person
$665
per person
found 1 day ago
The hotel needs to invest in a service elevator for their employees because there can only be five people on the elevator at a time and there’s 16 floors and it takes forever before you can catch an elevator.
Also, the room set up. The beds are super close to the wall in entryway so it makes it awkward to navigate. They need to make an adjustment. The sinks are super small with no room to really lay out your toiletries if needed..
The thermostat in my room in particular did not work even though a worker came in and tried to reset it and it was 40° in the room was reading 69° with no heat. Nobody came during the entire weekend to change the bedsheets to give us change switch out the trash. There was also no ironing board or iron in our rooms. Photographed shows robes in the rooms. There are no robes in the room. Everything we needed every time we had to calm down for them to bring it up.
Reviewed on May 4, 2026

4.0-star property
Level Chicago – Old Town
Downtown Chicago
9/10 Wonderful! (481 reviews)
Jul 15 - Jul 18
3 night stay
Boston (BOS) to Chicago (ORD)
Delta • Roundtrip • Coach
Save 100% on your flight
Price was $1,178, price is now $748 per person
$748
per person
found 1 day ago
We always love staying here. Such great service and nice accommodations.
Reviewed on Nov 20, 2025
Top rated hotels for your Chicago vacation package

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
0.43 mi from city center
$136 nightly
The price is $162 total per night
$162 total
Jun 29 - Jun 30
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 securing valuables, concierge services, and luggage storage. Additional amenities include conference space, a business center, and express check-out.

Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Free Cancellation
Reserve now, pay when you stay
13.75 mi from city center
$135 nightly
The price is $154 total per night
$154 total
Jun 28 - Jun 29
Total with taxes and fees
At Hyatt Regency O'Hare Chicago, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. If you drive, self parking is USD 45 per night, or you can take advantage of the free airport shuttle (available 24 hours). Multilingual staff at the front desk are standing by 24/7 to help with luggage storage, securing valuables, and tours or tickets. Additional amenities include conference space, a business center, and a microwave in a common area.

Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Free Cancellation
Reserve now, pay when you stay
15.67 mi from city center
$208 nightly
The price is $244 total per night
$244 total
Jul 3 - Jul 4
Total with taxes and fees
Guests of Hilton Chicago O'Hare Airport enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is USD 77 per day if you plan to drive, or hop aboard the free airport shuttle (available on request). Multilingual staff at the front desk are standing by 24/7 to help with concierge services, luggage storage, and securing valuables. Additional amenities include a conference center, a business center, and a computer station.
Lowest 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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