Cortland Holidays
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Top Flight + Hotel Deals in Cortland
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was €1,009, price is now €529 per person
€529
per person
20 Nov - 27 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.
Reviewed on 16 Oct 2025
Arlo Chicago
Downtown Chicago
Price was €828, price is now €452 per person
€452
per person
20 Nov - 27 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
I had a wonderful stay! The staff was kind and attentive, the room was spotless and comfortable, and the location was perfect for exploring the area.
Reviewed on 21 Oct 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was €763, price is now €433 per person
€433
per person
20 Nov - 27 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel
Reviewed on 20 Oct 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was €776, price is now €463 per person
€463
per person
20 Nov - 27 Nov
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (2,188 reviews)
Food from restaurant wasn’t fresh and was a little overpriced. Also check in is at 4:00 pm which is inconvenient if you reach early. Had to pay extra for early check in at 12:00 noon.
Reviewed on 20 Oct 2025
Top hotels in Cortland
Quality Inn and Suites St Charles - West Chicago
1600 E Main St, St. Charles, IL
Fully refundableReserve now, pay when you stay
The price is €65 per night from 20 Nov to 21 Nov
€65
20 Nov - 21 Nov
includes taxes & fees
8/10 Very Good! (1,019 reviews)
"Rooms are comfortable. Very convenient to downtown St. Charles"
Reviewed on 17 Oct 2025
Red Roof Inn & Conference Center Chicago - N Aurora/ Naperville
201 Smoke Tree Plaza Dr, Building A, North Aurora, IL
Fully refundableReserve now, pay when you stay
The price is €60 per night from 27 Oct to 28 Oct
€60
27 Oct - 28 Oct
includes taxes & fees
7.2/10 Good! (366 reviews)
"Yes clean and safe"
Reviewed on 17 Oct 2025
Days Inn by Wyndham St. Charles IL
1635 E Main St, St. Charles, IL
Fully refundableReserve now, pay when you stay
The price is €61 per night from 26 Oct to 27 Oct
€61
26 Oct - 27 Oct
includes taxes & fees
7.4/10 Good! (1,010 reviews)
"Our room was very nice, modern and very clean. The staff was eager to please. We requested adjoining rooms for family, and they made it happen."
Reviewed on 13 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
