Flights To Stephenson County - Cheap Flights Starting at

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Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

Jan 11 - Jan 18

7 night stay

Calgary (YYC) to Chicago (ORD)

United • Roundtrip • Coach
Price was CA $1,287, price is now CA $929 per person
CA $929
per person
found 2 hours ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Nov 27 - Nov 30

3 night stay

Toronto (YYZ) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was CA $2,144, price is now CA $1,505 per person
CA $1,505
per person
found 1 day ago
Hotel Saint Clair- Magnificent Mile
4.0-star property

Hotel Saint Clair- Magnificent Mile

Jan 11 - Jan 18

7 night stay

Calgary (YYC) to Chicago (ORD)

United • Roundtrip • Coach
Price was CA $1,542, price is now CA $1,148 per person
CA $1,148
per person
found 2 hours ago
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Travelers ❤️ These Stephenson County 🏨

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
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.
Opens in a new windowCountry Inn & Suites by Radisson, Freeport, IL
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! (398 reviews)
"Our experience at this Super 8 was extremely disappointing. The hotel was dirty, the facilities were outdated, and the maintenance was very poor. However, the worst part of our stay was what happened to our 4-year-old son. After eating breakfast at the hotel, he developed vomiting and diarrhea that ..."

Reviewed on Oct 16, 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! (494 reviews)
"Breakfast buffet was good"

Reviewed on Oct 18, 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.