Freeport Vacations from $340
Book a Hotel + Flight or Car together to unlock savings
Your Freeport Vacation
Cuisine, art, entertainment and more … There's so much to experience with a Freeport vacation package. And with the ability to easily customize your city adventure, it's guaranteed to be one that's difficult to forget. Fill your free time with visits to Krape Park, Winneshiek Playhouse and Silver Creek Museum, some of the attractions you simply have to see during a trip to Freeport. Expedia is here to help you escape your routine. Tailor your vacation to Freeport to suit your travel style, whatever that may look like.
The Latest Freeport Vacation Packages
- THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Jan 15 - Jan 19THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel + Flight
Downtown Chicago4 nights4.0 star property8.6/10 - Excellent (1,000 reviews)"Roman everything was clean everything was made that was all and it was very"Reviewed November 4, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop$530$340found 1 day agoper traveler - The Emily Hotel
Dec 24 - Dec 29The Emily Hotel + Flight
Downtown Chicago5 nights4.0 star property9.2/10 - Wonderful (1,356 reviews)"Staff was friendly and the room was clean"Reviewed November 3, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Hotel Riu Plaza Chicago
Jan 5 - Jan 10Hotel Riu Plaza Chicago + Flight
Downtown Chicago5 nights4.0 star property9.4/10 - Exceptional (5,642 reviews)"Excellent hotel in an excellent location. Close to all the attractions. Fabulous size room with the most comfiest bed! All the amenities you need are already in the room. Only complaint was the shower pressure was low. Other than that it was fabulous. Excellent breakfast included - fantastic selection! Would definitely recommend this hotel."Reviewed November 4, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop$678$426found 1 day agoper traveler - Level Chicago Fulton Market
Jan 5 - Jan 10Level Chicago Fulton Market + Flight
Downtown Chicago5 nights4.0 star property9.2/10 - Wonderful (602 reviews)"If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa. There was no housekeeping. Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before..."Reviewed November 4, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop$640$404found 1 day agoper traveler - Hotel Saint Clair- Magnificent Mile
Jan 15 - Jan 19Hotel Saint Clair- Magnificent Mile + Flight
Downtown Chicago4 nights4.0 star property8.6/10 - Excellent (2,373 reviews)"Property was fine. It was very noisy. Needs soundproofing Front staff not overly friendly."Reviewed November 4, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop$536$350found 1 day agoper traveler
Where to stay near Freeport
Cedarville
Discover Cedarville, a welcoming destination perfectly suited for families and outdoor enthusiasts looking for a blend of adventure and city charm. With attractions like the serene Krape Park, the engaging Freeport Art Museum, and the historic Stephenson County Historical Museum, there’s something for everyone to enjoy. Located about 7 miles by car from Freeport, Cedarville provides easy access to a variety of activities year-round, making it a smart choice for your stay.
Ridott
Experience the charm of Ridott, a great hub for family travelers and weekend getaway enthusiasts looking for a blend of outdoor adventure and local history. With attractions like the Stephenson County Historical Museum, Silver Creek Museum, and the scenic Oakdale Nature Preserve, there's something for everyone to enjoy. Located about 7 miles by car from Freeport, Ridott offers easy access to both relaxation and exploration, making it a smart choice for your next stay.
Dakota
Make the most of your visit by staying in Dakota, a haven for families and nature lovers thanks to its rich outdoor activities and scenic beauty. You’ll enjoy easy access to the nearby national state park and local landmarks like the Stephenson County Historical Museum and the Freeport Art Museum. Located about 8 miles by car from Freeport, Dakota offers a budget-friendly option for travelers seeking adventure and relaxation. Choosing Dakota for your stay ensures a memorable getaway in a charming setting.
Lena
Lena stands out as a prime spot for family and budget travelers interested in outdoor adventures and picturesque scenery. This charming city offers easy access to attractions like Apple River Canyon State Park, where you can explore nature trails, and SplashLand Family Water Park, perfect for a fun-filled day with the kids. Just about a 13-mile drive from Freeport, Lena is a smart choice for travelers seeking a blend of relaxation and recreation in a welcoming atmosphere.
German Valley
Travelers seeking a charming getaway will find German Valley to be the ideal base for their vacation, featuring a delightful blend of family-friendly activities and natural beauty. With attractions like Oakdale Nature Preserve, where you can immerse yourself in the outdoors, and the Silver Creek Museum and Stephenson County Historical Museum, rich in local history, there's something for everyone. Located about 13 miles by car from Freeport, German Valley offers an inviting atmosphere for a memorable stay.
Discover the most popular places to visit in Freeport
Freeport Hotel Deals
Country Inn & Suites by Radisson, Freeport, IL
Country Inn & Suites by Radisson, Freeport, IL
"Breakfast buffet was good"
City Express By Marriott Freeport
City Express By Marriott Freeport
Country Inn & Suites by Radisson, Stockton, IL
Country Inn & Suites by Radisson, Stockton, IL"The weekend breakfast cooked to order is an interesting idea except when you’re not the first ones there. Fortunately there were other things to eat while we waited. Breakfast was pretty good except for the extremely salty sausages."
"Great place in a great town."
Frequently Asked Questions
How much does a Freeport vacation package cost?
You'll find cheap prices from $340 on Expedia for your Freeport escape. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Freeport costs.
What are the cheapest months to go to Freeport?
You can typically find reduced prices and better availability in August, September and December. Browse our cheap Freeport vacation packages and you could score some great off-season deals.
How many days is enough for Freeport?
The ideal duration of your Freeport vacation depends on what you'd like to see. Usually, a handful of days to a week will give you plenty of time to visit all the top attractions and discover some hidden spots along the way.
Is it worth booking a vacation package to Freeport?
Known for its golfing and home to leading attractions like Krape Park, a Freeport vacation is bound to impress. Another highlight to check out? Don't miss Little Cubs Field.
How to find the best Freeport package deals?
Begin your search for a Freeport package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Freeport package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Freeport getaway off to a flying start.
Is it cheaper to book a Freeport vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component separately. And you'll still get the flexibility to create a customized Freeport vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Freeport?
If you're considering an impromptu Freeport trip, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land awesome deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Freeport vacation packages?
If you're like us, you love traveling but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Freeport break across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.