Winslow Holidays from £1,174

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Your Winslow Holiday

Take the worry out of organising your next exciting adventure with a Winslow holiday package. Whether you're lured here by its landmarks, food or other highlights, there's a never-ending supply of new experiences to be had. Need some ideas on what to do or see first during your trip to Winslow? Head straight for leading attractions such as Lake Le Aqua Na State Park. Don't put off visiting this city any longer. The ultimate Winslow holiday is only a few clicks away with Expedia.

The Latest Winslow Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
16 Jul - 22 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (703 reviews)
The Art Deco architectural beauty of this hotel is stunning! Every time I was in the elevator area, I was wowed. We had a corner room on the 22nd floor and it was great. Lots of space and great art deco inspired furniture and lights. We had a view of the bridge and the lake. The breakfast at the French cafe was so so. Overall I highly recommend this hotel.

Reviewed on 30 May 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Jul - 22 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,212 reviews)
Bid room but not cleaned nor updated. Late check out is only at 1pm. No room upgrade offered. There was 1 day that room was not serviced until late evening. Good location

Reviewed on 2 Jun 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
16 Jul - 22 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Very friendly and helpfu

Reviewed on 31 May 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
16 Jul - 22 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (3,522 reviews)
Very nice hotel near everything in Chicago. The rooftop 10/10. Not problem at our stay only one thing. They offer us a room with view at the river but the room wasn’t available until almost 6pm when the check in is 4pm .

Reviewed on 3 Jun 2024

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
22 Aug - 30 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Very nice, clean, large rooms. Well-appointed. Hotel lobby very welcoming. Looked like a lovely outdoor dining patio, though I didn’t eat there.

Reviewed on 22 May 2024

Ambassador Chicago, part of JdV by Hyatt

Ambassador Chicago, part of JdV by Hyatt

4 out of 5
Downtown Chicago
per person
22 Aug - 30 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.8/10 Excellent! (1,009 reviews)
Love the seperate living room. Amazing view. Do need vending machines or something though.

Reviewed on 4 Jun 2024

Winslow Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Lake Le Aqua Na State Park, Famous Fossil Winery and Stagecoach Golf Course

Our pick of the best Winslow Hotel Deals

Super 8 by Wyndham Monroe WI
Super 8 by Wyndham Monroe WI
2 out of 5
500 6th St and Hwy 69, Monroe, WI
Stay at this business-friendly motel in Monroe. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
8.8/10 Excellent! (610 reviews)
Comfortable Stay
"The room was on the smaller side but was clean, with a comfortable bed and recliner. The toilet/tub area was small and separate from the sink area in the room. The internet was fast also. The breakfast was mostly cold offerings along with biscuits and gravy. This was our first stay at a Super 8 and ..."

Reviewed on 19 May 2024

Super 8 by Wyndham Monroe WI
Country Inn & Suites by Radisson, Stockton, IL
Country Inn & Suites by Radisson, Stockton, IL
2.5 out of 5
200 Dillon Ave, Stockton, IL
Stay at this business-friendly hotel in Stockton. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (483 reviews)
"Pool hours not very accomadationg"

Reviewed on 24 May 2024

Country Inn & Suites by Radisson, Stockton, IL
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 Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. Popular ...
8.8/10 Excellent! (692 reviews)
Pec Thing stay
"We always stay here when coming for the Pec flea market. Great place to stay but the price the last few years has made this very expensive compared to other hotels in the area."

Reviewed on 23 May 2024

Country Inn & Suites by Radisson, Freeport, IL
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 Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Winslow travel package cost?
Starting from a low £1,174, a travel package is your gateway to low-cost travel. Customize your Winslow trip by choosing from our comprehensive range of hotels, flights and rental cars.
If I'm not able to travel, can I cancel my Winslow travel package?
Whether it’s your hotel or flight, you can cancel or change it. Locked in your Winslow travel package in the last 24 hours? You may be able to make changes for free. If it’s been longer than that, you may incur a fee from your airline, hotel or car rental company. For more information, visit our Customer Service Portal. We’ll help you each step of the way.
How do I get a cheap travel package to Winslow?
Book everything in the one place with our Winslow holiday packages. You’ll find deals on flights, hotels, tours and more that’ll keep your wallet happy and your adventurous spirit busy. And, with more than 550 airlines and 1,000,000 hotel options across the globe to select from, you have countless opportunities to mix and match all you want.
Does Expedia offer Book Now, Pay Later Winslow holidays?
We sure do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in instalments. Simply select the payment plan that suits you best during the checkout process and take away the stress of budgeting for your trip. Make sure you bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your travel buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: If paying bite-sized amounts each month sounds right for you, Klarna can help. Paying in convenient monthly instalments will make your holiday dreams possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay off your holiday across multiple transactions.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to hit that “book now” button, choose a low deposit holiday payment plan with Klarna.

What are the top hotels in Winslow?
Get your escape off to an excellent start by reserving a room at Hyatt Regency Chicago. It’s one of most sought-after hotels in Winslow. Another top option is The Godfrey Hotel Chicago.
How far in advance should I book my Winslow holiday?
Browse Expedia to compare international fares as soon as you know your travel dates. In most cases, you can purchase a seat up to a year in advance. If you can’t see your preferred carrier, or you have to book last minute, fear not. The lowest prices to Winslow sometimes appear a few weeks before the date of departure.
What does an Expedia Winslow travel package include?
Travel packages include flights, hotels and rental cars, but you can combine any of them to create your ideal Winslow trip. You can also add on activities and experiences once you’ve made your booking. You’re in the driver’s seat! When you bundle your bookings with Expedia, you’ll enjoy discounts you won’t find anywhere else.
What should I know before booking a Winslow travel package?
Whether it’s relaxation or adventure you’re chasing, a Winslow travel package lets you organise your escape your way. Plus, you’ll score great discounts when you combine your hotel with your flights and rental car. The more you bundle, the more you’ll save!
Can I choose my airline with a Winslow Expedia travel package?
With a travel package, you’re the one in charge. Whether you’re looking to fly to Winslow in economy or business class, simply pick from the available airline options. Expedia has access to over 550 airline partners throughout the world.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.