Cortland Vacations from $519

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.
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 $768, price is now $519 per person
$519
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,854 reviews)
Everything about my room was fine, other than it being quite small. The staff was very good. The only negative was the street noise. My room was on the 8th floor and even with the windows closed and the A/C running I could clearly hear horns and sirens on the street.

Reviewed on Jul 23, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,059, price is now $616 per person
$616
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,714 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,527, price is now $918 per person
$918
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (501 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,204, price is now $758 per person
$758
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (523 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $971, price is now $658 per person
$658
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,603 reviews)

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Cortland Hotel Deals

Days Inn by Wyndham St. Charles IL

Days Inn by Wyndham St. Charles IL

2.5 out of 5
1635 E Main St St. Charles IL
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $81 total per night from Aug 17 to Aug 18
$81 total
Aug 17 - Aug 18
Total with taxes and fees
7.4/10 Good! (1,001 reviews)
"Nothing was proper"

Reviewed on Jul 22, 2026

Days Inn by Wyndham St. Charles IL
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 refundable
$77 nightly
The price is $86 total per night from Aug 23 to Aug 24
$86 total
Aug 23 - Aug 24
Total with taxes and fees
8.2/10 Very Good! (1,004 reviews)
"Our family booked 4 rooms on a Saturday night. One of the rooms had a completely inoperable shower, with water squirting all over the ceiling only. Another room had a hole in the shower wall. My daughter was given a room key and upon opening the room found luggage and other personal items belonging ..."

Reviewed on Jul 23, 2026

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
$79 nightly
The price is $88 total per night from Jul 26 to Jul 27
$88 total
Jul 26 - Jul 27
Total with taxes and fees
Geneva Motel Inn
See all 136 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.

Find the Best Cortland Vacation Packages

Cortland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rockford, IL (RFD-Greater Rockford)
Population
4,300
Top Sights
Ellwood House Museum, Star Worlds Arcade and Northern Illinois University

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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 $519 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.