Flights To Stephenson County - Cheap Flights Starting at

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Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
3.5-star property

Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination

Sep 11 - Sep 14

3 night stay

Toronto (YYZ) to Chicago (ORD)

Air Canada • Roundtrip • Coach
Price was CA $1,051, price is now CA $760 per person
CA $760
per person
found 1 day ago
Pendry Chicago
4.5-star property

Pendry Chicago

Oct 1 - Oct 4

3 night stay

Toronto (YTO) to Chicago (ORD)

Porter Airlines • Roundtrip • Coach
Price was CA $1,653, price is now CA $1,151 per person
CA $1,151
per person
found 1 day ago
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

Aug 24 - Aug 28

4 night stay

Toronto (YTO) to Chicago (ORD)

Air Canada • Non-stop roundtrip • Coach
Price was CA $2,169, price is now CA $1,554 per person
CA $1,554
per person
found 7 hours 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! (914 reviews)
"Staff was very pleasant and helpful"

Reviewed on Jul 13, 2026

Opens in a new windowCountry Inn & Suites by Radisson, Freeport, IL
City Express By Marriott Freeport

City Express By Marriott Freeport

3 out of 5
1060 Riverside Dr Freeport IL
Book a stay at this business-friendly hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Winneshiek Playhouse and Lincoln-Douglas Debate Square are located nearby.
Opens in a new windowCity Express By Marriott 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! (375 reviews)
"My stay was good. My only request is updating lamps or an outlet to allow for charging with USB ports. I haven’t stayed any place in awhile that didn’t have this in rooms."

Reviewed on Jul 3, 2026

Opens in a new windowSuper 8 by Wyndham Freeport
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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! (482 reviews)
"The first time I was disappointed in a Hampton Inn. The staff was great but …. Dirty linens were laying in the hallway. Two guests asked for different rooms because of an odor in the room."

Reviewed on Jul 11, 2026

Opens in a new windowHampton Inn Freeport
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.