Winslow Vacation Packages

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Your Winslow Vacation

Memorable adventures await when you reserve a vacation package to Winslow. Whether you're a foodie, history buff or just a traveler who loves to discover new places, there's something for everyone in this awesome city. Any trip to Winslow has to include a little sightseeing. Lake Le Aqua Na State Park is a great place to begin exploring. Stop daydreaming and start traveling. Check out the range of options on Expedia today and put your Winslow vacation plans into motion!

Top Winslow Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Wade

The Wade

4.5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,066 reviews)
Beautiful place with amazing view! The room was amazing. The location was amazing. Staff helpful. Enjoyed stay. Will stay here again and again and again.

Reviewed on Jul. 28, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
The hotel was nice, staff were friendly and the overall stay was excellent and convenient to walk.

Reviewed on Jul. 28, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
I liked the hotel room's kitchen and it is very nice, however VERY small. The pool/amenities are also very nice. One major challenge was there was a last minute change to the location of our reservation from old town to fulton market. They did communicate the change and provided a discount, however, this occurred the day before our trip. The check-in process was also very disorganized and confusing. Information easily accessible in the reservation was not used, requiring extra check-in time. They told us a crib was available, and later found only a pack and play. I requested bedding for the pull out 4 times before someone brought them. Overall, management needs to improve their operations.

Reviewed on Jul. 21, 2025

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

4 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,004 reviews)
All staff were very friendly and helpful. Hotel was in convenient location for walking.

Reviewed on Jul. 27, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

Ready to book your vacation to Winslow?

 

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Winslow Hotel Deals

AmericInn by Wyndham Monroe

AmericInn by Wyndham Monroe

2.5 out of 5
424 4th Ave, Monroe, WI
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from Aug 17 to Aug 18
CA $170
CA $187 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (355 reviews)
"The room still smelled and looked new. And staff very nice."

Reviewed on Jul. 18, 2025

AmericInn by Wyndham Monroe
Super 8 by Wyndham Freeport

Super 8 by Wyndham Freeport

2 out of 5
1551 Sleezer Home Rd, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is CA $113 per night from Aug 3 to Aug 4
CA $113
CA $125 total
Aug 3 - Aug 4
includes taxes & fees
6.8/10 (330 reviews)
nicer than I expected
"I didnt go in expecting a lot, but the hotel was way nicer than I thought. Always thought "super 8" was just a cheap place, some might be, but this one was nice"

Reviewed on Jul. 17, 2025

Super 8 by Wyndham Freeport
Baymont by Wyndham Freeport

Baymont by Wyndham Freeport

2.5 out of 5
1060 Riverside Dr, Freeport, IL
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Aug 10 to Aug 11
CA $131
CA $145 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very Good! (672 reviews)
Good option in area
"Very nice Staff… Property a little rundown was the only reason I marked down one star. I would stay here again."

Reviewed on Jul. 26, 2025

Baymont by Wyndham Freeport
See all 97 properties in Winslow
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.
All Inclusive Vacations
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Beach Vacations
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Frequently asked questions

How much does a Winslow vacation package cost?
You'll find cheap prices from CA $960 on Expedia for your Winslow escape. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Winslow costs.
What are the cheapest months to go to Winslow?
January, February and November are great times to search for cheap Winslow vacation packages. Choosing to travel in quieter months means you'll typically find lower prices on flights and accommodations.
How many days is enough for Winslow?
The ideal length of your Winslow vacation depends on what you'd like to do. Usually, a few days to a week will give you enough time to hit all the main attractions and explore some hidden gems along the way.
How to find the best Winslow package deals?
Begin your search for a Winslow package deal by entering your destination and travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Winslow package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winslow escape underway.
Is it cheaper to book a Winslow vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Winslow vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Winslow?
Score amazing discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Winslow vacation.
How to plan a trip to Winslow?

  1. Choose when to get away: Check your schedule and get packing. Your preferred season and the activities on offer will also help you decide when to visit Winslow.
  2. Set a budget: Consider costs such as flights, meals and transportation when working out how much to set aside for your trip to Winslow. Then, choose a hotel that works with your budget, whether that's an affordable option or a swankier getaway.
  3. Work out your trip length: Think about how much time you'd like to spend exploring Winslow. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find a Winslow vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.