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Price found within the past 48 hours. Click for updated prices.

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was €708, price is now €437 per person
€437
per person
20 Nov - 25 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Clean room, friendly staff, great location and within walking distance from all shops!
Reviewed on 7 Oct 2025

Pendry Chicago
Downtown Chicago
Price was €815, price is now €456 per person
€456
per person
20 Nov - 25 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
The bed was extremly comfortable Staff was very attentive. Highly recommend
Reviewed on 7 Oct 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,875, price is now €1,050 per person
€1,050
per person
20 Nov - 25 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.
Reviewed on 6 Oct 2025

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €767, price is now €518 per person
€518
per person
20 Nov - 25 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (3,344 reviews)
Clean room and very nice amenities. We loved being so close to everything.
Reviewed on 9 Oct 2025

Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Price was €703, price is now €485 per person
€485
per person
20 Nov - 25 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (1,035 reviews)
The only things I didn’t care for was the unexpected $129 charge when checking in. Destination fee? Like I didn’t pay enough for the room, I get charged an extra fee that was not disclosed while booking. I wouldn’t have stayed there if I knew there was a “destination” fee. They gave us a $15 food credit. The breakfast was $30 a plate so pretty much a useless credit. The room was nice, however, I will not be returning to this hotel.
Reviewed on 5 Oct 2025
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was €1,875, price is now €1,050 per person
€1,050
per person
20 Nov - 25 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.
Reviewed on 6 Oct 2025

The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd, Willowbrook, IL
The price is €103 per night from 13 Oct to 14 Oct
€103
13 Oct - 14 Oct
includes taxes & fees
Stay at this 3.5-star boutique hotel in Willowbrook. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,281 reviews)
Couples like: adults-only property, hot tub, fireplace, romance packages available
Travellers say...
"Loved this place"
Reviewed on 10 Oct 2025

LondonHouse Chicago, Curio Collection by Hilton
85 East Wacker Drive, Chicago, IL
The price is €176 per night from 30 Oct to 31 Oct
€176
30 Oct - 31 Oct
includes taxes & fees
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our ...
9.4/10 Exceptional! (3,351 reviews)
Couples like: full-service spa, couples spa treatments, bar
Travellers say...
"Nice river view, very comfortable beds and linens, central to shopping, restaurants & the beautiful river walk. Great stay for first time in Chicago."
Reviewed on 4 Oct 2025

Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
The price is €204 per night from 30 Oct to 31 Oct
€204
30 Oct - 31 Oct
includes taxes & fees
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,997 reviews)
Couples like: full-service spa, couples spa treatments, happy hour
Travellers say...
"Put in new carpet and update walls"
Reviewed on 6 Oct 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.