Cortland Vacations from $398

Book a Hotel + Flight or Car together to unlock savings

Your Cortland Vacation

Excellent adventures await when you reserve a vacation package to Cortland. Whether you're a foodie, art enthusiast or just a traveler who loves experiencing new places, there's something for everyone in this lively city. Make your trip to Cortland even more exciting by including some sightseeing. Northern Illinois University, Huskie Stadium and Ellwood House Museum are some of the big attractions worth exploring. Don't put off exploring this city any longer. Your ultimate Cortland vacation is a couple of clicks away with Expedia.

The Latest Cortland vacation packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was $948, price is now $398 per person
$398
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on Aug 25, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,362, price is now $675 per person
$675
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on Aug 22, 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $817, price is now $412 per person
$412
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
Excellent staff very friendly

Reviewed on Aug 29, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,000, price is now $518 per person
$518
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on Aug 27, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $990, price is now $520 per person
$520
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,342 reviews)
Liked everything. Appreciated later check out time. Front desk very helpful. Breakfast was⭐️🌟🥇

Reviewed on Aug 29, 2025

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Cortland Hotel Deals

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
$70 nightly
The price is $78 total per night from Sep 28 to Sep 29
$78 total
Sep 28 - Sep 29
Total with taxes and fees
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
$80 nightly
The price is $90 total per night from Aug 31 to Sep 1
$90 total
Aug 31 - Sep 1
Total with taxes and fees
Geneva Motel Inn
Red Roof Inn & Conference Center Chicago - N Aurora/ Naperville

Red Roof Inn & Conference Center Chicago - N Aurora/ Naperville

2 out of 5
201 Smoke Tree Plaza Dr, Building A, North Aurora, IL
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $75 total per night from Sep 3 to Sep 4
$75 total
Sep 3 - Sep 4
Total with taxes and fees
Red Roof Inn & Conference Center Chicago - N Aurora/ Naperville
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.

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Frequently asked questions

How much does a Cortland vacation package cost?
You can pick up a vacation package to this destination from $398 on Expedia. But how much your vacation 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 usually find lower rates and better availability in March, November and December. Explore our cheap Cortland vacation packages and you could get some great off-season discounts.
How many days is enough for Cortland?
With a well-organized itinerary, you can easily visit the main Cortland sights in a handful of days. But if you prefer to venture off the beaten track or go on day trips, consider booking your Cortland vacation for longer.
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 vacation as a package?
You can enjoy significant savings on your next Cortland escape by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to view some great hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Cortland vacation packages?
Set off on your ideal getaway to Cortland with Expedia's Book Now, Pay Later vacations. There's no need to save up or wait for your next payday — we've teamed up with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily stick to your budget and snap up travel deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.