Cortland Holidays

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Top Flight + Hotel Deals in Cortland

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was €1,169, price is now €779 per person
€779
per person
2 Nov - 7 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,008 reviews)
The service was excellent, they made my birthday very special!

Reviewed on 19 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,927, price is now €1,160 per person
€1,160
per person
2 Nov - 7 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,807, price is now €1,195 per person
€1,195
per person
10 Oct - 14 Oct
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Great spot, good location, nice rooms.

Reviewed on 20 Aug 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,713, price is now €1,140 per person
€1,140
per person
10 Oct - 14 Oct
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
Staff were excellent, I needed to mail some parcels for a business event which they held for over a week (arrived earlier than expected!) breakfast was also excellent. Rooms were noisy, not from outside but from the other rooms. Walls must be thin and could hear conversation and the TV from both sides.

Reviewed on 20 Aug 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was €1,782, price is now €1,218 per person
€1,218
per person
2 Nov - 7 Nov
found 17 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on 12 Aug 2025

Top hotels in Cortland

Quality Inn and Suites St Charles - West Chicago

Quality Inn and Suites St Charles - West Chicago

2.5 out of 5
1600 E Main St, St. Charles, IL
Fully refundableReserve now, pay when you stay
The price is €68 per night from 21 Sept to 22 Sept
€68
21 Sept - 22 Sept
includes taxes & fees
8/10 Very Good! (1,009 reviews)
"It was an ok stay. Seemed to be part of the original hotel so dated and minor maintenance things. Brought it up to the desk when leaving and they were quite pleasant about it snd no doubts itvwas taken care of. Nice to know there is a pet friendly place near our daughters place."

Reviewed on 18 Aug 2025

Quality Inn and Suites St Charles - West Chicago
Geneva Motel Inn

Geneva Motel Inn

2 out of 5
100 South Tyler Rd, St. Charles, IL
Fully refundableReserve now, pay when you stay
7.2/10 Good! (921 reviews)
"Nice place fir the price"

Reviewed on 20 Aug 2025

Get rates
Geneva Motel Inn
Country Inn & Suites by Radisson, Sycamore, IL

Country Inn & Suites by Radisson, Sycamore, IL

2.5 out of 5
1450 South Peace Road, Sycamore, IL
Fully refundable
The price is €88 per night from 31 Aug to 1 Sept
€88
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (865 reviews)
"The bed was super comfortable. The pillows were amazing."

Reviewed on 10 Aug 2025

Country Inn & Suites by Radisson, Sycamore, IL
See all 131 properties in Cortland
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.

Frequently asked questions

How much does a Cortland holiday package cost?
You can pick up a holiday package to this destination from €779 on Expedia. But how much your holiday to Cortland costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Cortland?
You can typically find lower rates and greater availability in January, February and April. Browse our cheap Cortland holiday packages and you could score some great off-season discounts.
How many days is enough for Cortland?
Generally, a handful of days is enough to tick off the major attractions during your Cortland holiday. However, if you prefer to have time to chill out or go on day trips, think about extending your trip.
How to find the best Cortland package deals?
Begin your search for a Cortland package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Cortland package deal right away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Cortland escape underway.
Is it cheaper to book a Cortland holiday as a package?
You can enjoy significant savings on your next Cortland escape by booking a customised holiday package. Click on the "Package" heading, then select your destination and travel dates to view some great hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Cortland?
Secure incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Cortland break.
How to plan a trip to Cortland?

  1. Pick your dates: The things you'd like to do in Cortland and your favourite season can help you decide when to travel.
  2. Set a budget: Factor in costs such as transportation, flights and meals when calculating how much to set aside for your trip to Cortland. Then, choose a property that matches your budget, whether that's an economical option or a lavish getaway.
  3. Set the duration of your trip: Start by making a list of all the activities and sights you want to get to in Cortland. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalised Cortland holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.