Flights To Stephenson County - Cheap Flights Starting at

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Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

Aug 6 - Aug 10

4 night stay

Toronto (YYZ) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was CA $1,992, price is now CA $1,294 per person
CA $1,294
per person
found 6 hours ago
Swissotel - Chicago
4.5-star property

Swissotel - Chicago

Aug 22 - Aug 29

7 night stay

Toronto (YYZ) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was CA $2,582, price is now CA $1,523 per person
CA $1,523
per person
found 1 day ago
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

Aug 22 - Aug 29

7 night stay

Toronto (YYZ) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was CA $3,247, price is now CA $2,082 per person
CA $2,082
per person
found 1 day ago
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Travelers ❤️ These Stephenson County 🏨

Country Inn & Suites by Radisson, Freeport, IL

Country Inn & Suites by Radisson, Freeport, IL

2.5 out of 5
1710 South Dirck Drive Freeport IL
Stay at this hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Little Cubs Field and Krape Park Carousel are located nearby.
9/10 Wonderful! (899 reviews)
"The hotel and propert clean. Room nice. Just wish there was shower curtain on shower pole. Everything else was nice. We had handicap room. 235."

Reviewed on Jun 1, 2026

Opens in a new windowCountry Inn & Suites by Radisson, Freeport, IL
Hampton Inn Freeport

Hampton Inn Freeport

2.5 out of 5
109 S Galena Ave Freeport IL
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free parking, and a 24-hour fitness center. Popular attractions Winneshiek Playhouse and Lincoln-Douglas Debate Square are located nearby.
8.8/10 Excellent! (474 reviews)
"Always stay here when coming to Freeport. Clean rooms, decent breakfast."

Reviewed on May 30, 2026

Opens in a new windowHampton Inn Freeport
Super 8 by Wyndham Freeport

Super 8 by Wyndham Freeport

2 out of 5
1551 Sleezer Home Rd Freeport IL
Stay at this hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Stephenson County Historical Museum and Oscar Taylor Home are located nearby.
7/10 Good! (361 reviews)
"First time at a Super 8. And it was really nice and staff was wonderful. Great location. Will stay again."

Reviewed on May 24, 2026

Opens in a new windowSuper 8 by Wyndham Freeport
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Peace & Simplicity in a Little Red Cabin on the Farm

Peace & Simplicity in a Little Red Cabin on the Farm

Lena IL
Stay at this cabin in Lena. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Lake Le Aqua Na State Park and Stagecoach Golf Course are located nearby.
10/10 Exceptional! (25 reviews)
"I had a wonderful stay in this charming little red cabin. It was fully equipped, and I had everything I needed to feel comfortable. The place was cozy and well maintained. I highly recommend it!"

Reviewed on Jun 1, 2026

Opens in a new windowPeace & Simplicity in a Little Red Cabin on the Farm
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 is the cheapest flight to Stephenson County?
For an idea of fares, the cheapest roundtrip flight to Stephenson County was during the last seven days. An easy way to snap up a good deal is to be flexible with your dates. This price was available on Travelocity for flights to Stephenson County departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Stephenson County?
For your biggest chance at grabbing a fabulous flight deal, organize your break in . Based on Travelocity's direct flight demand from January to December last year, it's the most affordable period to jet to Stephenson County.
How can I check my flight status to Stephenson County?
There are a few helpful ways to look up the status of your flight. You can find all the details you need in our Trips portal, which is located at the top of our homepage. Log in or open an account — you can then access and make changes to your bookings whenever you please. If you're already traveling, the Travelocity app can also help you look up the status of your flight to Stephenson County, as well as share details with any members of your family flying with you.
How do I find the best deals on flights to Stephenson County?
Try these tips — book ahead of time, avoid the peak tourist season and be flexible with your travel dates. If you don't have a specific date in mind, search for your flight to Stephenson County on Travelocity and click on "Flexible dates" at the top of the page. This will help you find any cheaper fares on surrounding days. was the most affordable price for a return flight to Stephenson County in the last seven days. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Stephenson County with Travelocity?
An amazing getaway is at the click of a button when you book your trip with Travelocity. With a wide selection of choices and competitive deals on cheap family flights, hotels, activities and rental cars, we make it easy to locate the best prices for you. You can also take advantage of our 24/7 customer support and free cancellation policies on most hotels throughout every stage of the process. Wander with us and reserve your cheap flights to Stephenson County today.
What are the most popular flight routes to Stephenson County?
Whether you're thinking about a short break or a lengthy vacation, we'll help you find your perfect flight to Stephenson County. Well-known flight routes to this destination include:

  • Denver, CO (DEN-Denver Intl.) to O'Hare Intl. Airport (ORD) - 4,203 flights a month.
  • Minneapolis, MN (MSP-Minneapolis - St. Paul Intl.) to O'Hare Intl. Airport (ORD) - 4,155 flights a month.
  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 4,138 flights a month.

How much is a flight to Stephenson County on average?
Based on prices found on Travelocity over the last seven days, roundtrip flights to Stephenson County were between and . Whenever you're ready to jet off, Travelocity will help you find a fare that'll match your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.