Winslow Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,448, price is now CA $1,013 per person
CA $1,013
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,714 reviews)
The room and hotel exceeded my expectations. The hotel was located in the best spot. I would definitely stay here again.

Reviewed on Jul 18, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $3,056, price is now CA $2,013 per person
CA $2,013
per person
Sep 22 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (501 reviews)
Level hotels are awesome

Reviewed on Jul 18, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,484, price is now CA $1,026 per person
CA $1,026
per person
Sep 4 - Sep 7
found 18 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Nice staff, easy check-in, and about an 8 minute walk to red line which can get you all over town. No complaints about our stay.

Reviewed on Jul 18, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $3,157, price is now CA $2,244 per person
CA $2,244
per person
Oct 8 - Oct 12
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Price was CA $2,160, price is now CA $1,546 per person
CA $1,546
per person
Sep 22 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (657 reviews)
The hotel is very modern and clean. The staff was very friendly and courteous. There was ample parking and plenty of places to grab a bite to eat within walking distance. The AC worked well and the bedding was very comfortable. I would definitely recommend this hotel to anyone looking to stay near the United Center.

Reviewed on Jul 18, 2026

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Winslow Hotel Deals

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
Fully refundable
The price is CA $177 per night from Jul 22 to Jul 23
CA $177
CA $197 total
Jul 22 - Jul 23
includes taxes & fees
9/10 Wonderful! (914 reviews)
"Staff was very pleasant and helpful"

Reviewed on Jul 13, 2026

Country Inn & Suites by Radisson, Freeport, IL
Country Inn & Suites by Radisson, Stockton, IL

Country Inn & Suites by Radisson, Stockton, IL

2.5 out of 5
200 Dillon Ave Stockton IL
The price is CA $123 per night from Aug 11 to Aug 12
CA $123
CA $137 total
Aug 11 - Aug 12
includes taxes & fees
8.4/10 Very good! (686 reviews)
"Needs a little updating and carpet either needs to be cleaned or replaced in the hallway. Overall we were comfortable but it could use some TLC such as replace some light bulbs in the bathroom and update the bedding. Staff that did the continental breakfast were friendly and kept that room clean. ..."

Reviewed on Jul 16, 2026

Country Inn & Suites by Radisson, Stockton, IL
Super 8 by Wyndham Monroe WI

Super 8 by Wyndham Monroe WI

2 out of 5
500 6th St and Hwy 69 Monroe WI
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Aug 10 to Aug 11
CA $118
CA $129 total
Aug 10 - Aug 11
includes taxes & fees
Super 8 by Wyndham Monroe WI
See all 104 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.
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Frequently asked questions

How much does a Winslow vacation package cost?
You'll find cheap prices from CA $1,013 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.

Explore a world of travel with Expedia

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