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3.0-star property
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
8.4/10 Very Good! (3,631 reviews)
Oct 4 - Oct 6
2 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Great place will stay again
Reviewed on Jul 27, 2025

5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
9.4/10 Exceptional! (1,679 reviews)
Oct 4 - Oct 6
2 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!
Reviewed on Jun 16, 2025

4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
9.4/10 Exceptional! (2,270 reviews)
Oct 10 - Oct 12
2 night stay
Boston (BOS) to Chicago (ORD)
American Airlines • Non-stop • Coach
Chicago (ORD) to Boston (BOS)
United • Non-stop • Coach
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per person
found 20 hours ago
Very convenient to the heart of Chicago!
Nice hotel!
Reviewed on Jul 24, 2025

3.5-star property
Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
8.8/10 Excellent! (2,571 reviews)
Oct 4 - Oct 6
2 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
I was traveling with two 14 year olds on a business/vacation trip and we stayed here for five days. The location is great. I wanted a hotel that was convenient to the major attractions and downtown, and safe for the boys to walk around on their own. We were able to walk to Navy Pier, Millennium Park, the Loop, and the Hancock Building. It's a good 20-25 minute walk to Navy Pier, but you walk along Lakeshore Drive and it's very enjoyable.
The property is very nice, although we didn't get the two beds that we selected through Orbitz.
The hotel is on the red line, so not as convenient to the airport as a hotel on the blue line. Parking here is pricey.
If you stay here, Hendrickx Belgian Belgian Bread Crafter is around the corner and an absolute must visit. Wildberry is on the other side and also very good.
The Hancock Building is a two minute walk. If you love city views, the 360 experience is worth a visit, and is less crowded than the Willis Tower. We did the Tilt experience and it was not worth the money.
If you go to Chicago and haven't gone on an architectural boat tour, this is an absolute MUST. Be sure to choose a tour affiliated with the Chicago Architectural Center because that's a nonprofit worth supporting AND the guides are amazing. It's a 20 minute walk from the hotel and you walk along MichiganAve., which rivals Fifth Avenue in New York for window shopping, retail, artwork, and restaurants.
Love, love, love Chicago and would stay at this property again.
Reviewed on Jul 29, 2025

3.0-star property
Courtyard by Marriott Chicago Magnificent Mile
Downtown Chicago
8.8/10 Excellent! (1,498 reviews)
Sep 12 - Sep 15
3 night stay
Boston (BOS) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
I felt it was all so confusing there. The parking is horrendous. You get an email stating 45 a night for self park but it’s 65-this is directly from the hotel. I ordered my room through Orbitz. Don’t get insurance through Orbitz as the hotel charges insurance as well. Expect a hold fee for incidentals of 70 a night. The room was clean. But minor scuffs. I took photos to make sure a charge didn’t come back to me. Bus is the way to go as the city is overpriced on uber. Orbitz does not match the hotel price be aware. It would seem like my issue is with Orbitz but it’s the hotel with all the surprise fees. If you’re looking for a clean hotel this is it. If you’re looking for friendly staff this isn’t it. If you offer someone something like water then you should offer everyone, I work in property management and if I offered someone something and not the next it would be a problem. Just saying. The pool is small. And right next to the gym and on the 10th floor. We were on the 18th and it wasn’t bad but just ok. Would I stay again probably not. I am big on friendly staff. Park other places as you can find way cheaper. We stayed for 3 nights. 195 total. Photos attached are the day we left. I don’t play when it comes to picking up behind myself.
Reviewed on May 25, 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
$161 nightly
The price is $189 total per night
$189 total
Sep 1 - Sep 2
Total includes 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

Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.05 mi from city center
$198 nightly
The price is $229 total per night
$229 total
Aug 22 - Aug 23
Total includes taxes and fees
Guests of Palmer House a Hilton Hotel enjoy a full-service spa, an indoor pool, and a 24-hour gym. Parking is available for USD 57 per night (USD 85 per night for valet parking), and there's also limo/town car service. Multilingual staff at the front desk are standing by 24/7 to help with access to locker space, luggage storage, and dry cleaning/laundry. Other amenities at this luxury hotel include a conference center, a business center, and express check-in.
Pool
Spa

Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
Free Cancellation
0.98 mi from city center
$142 nightly
The price is $167 total per night
$167 total
Aug 24 - Aug 25
Total includes taxes and fees
Guests of Crowne Plaza Chicago West Loop by IHG enjoy a gym, free WiFi in public areas, and conference space. Self parking is offered for USD 54.00 per day. Multilingual staff at the 24-hour front desk can assist with securing valuables, dry cleaning/laundry, and luggage storage. Additional amenities include a 24-hour business center, express check-in, and express check-out.
Pet friendly
Free WiFi
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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