Deals on vacations and trips to Winslow

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Winslow flight + hotel vacation packages

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
Save 100% on your flight
Price was $659, price is now $325 per person
$325
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,473, price is now $537 per person
$537
per person
Dec 23 - Dec 28
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.
The French Country Inn Lake Geneva

The French Country Inn Lake Geneva

3 out of 5
Price was $812, price is now $376 per person
$376
per person
Dec 16 - Dec 22
found 16 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A private beach and a restaurant are featured at this smoke-free hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, luggage storage, and concierge services are also on offer.
Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $1,020, price is now $524 per person
$524
per person
Dec 31 - Jan 3
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A full-service spa and a hot tub are featured at this luxury aparthotel. Enjoy the a rooftop terrace and perks like free self parking and a free airport shuttle. Free WiFi in public areas, a garden, and a lobby fireplace are also on offer.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $635, price is now $339 per person
$339
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Top Winslow hotels 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
Free Cancellation
$119 nightly
The price is $132 total per night
$132 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features an indoor pool and a gym. Enjoy the hot tub and free perks like full breakfast and free self parking. A business center, free WiFi in public areas, and a lobby fireplace are also on offer.
Pool
Hot Tub
Country Inn & Suites by Radisson, Stockton, IL

Country Inn & Suites by Radisson, Stockton, IL

2.5 out of 5
200 Dillon Ave, Stockton, IL
$77 nightly
The price is $86 total per night
$86 total
Oct 28 - Oct 29
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like self-serve breakfast and free self parking.
Pool
Breakfast included
Darlington Inn

Darlington Inn

2 out of 5
201 Christiensen Dr, Darlington, WI
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $86 total per night
$86 total
Oct 19 - Oct 20
Total with taxes and fees
This motel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Baymont by Wyndham Freeport

Baymont by Wyndham Freeport

2.5 out of 5
1060 Riverside Dr, Freeport, IL
Free Cancellation
Reserve now, pay when you stay
$77 nightly
The price is $85 total per night
$85 total
Nov 6 - Nov 7
Total with taxes and fees
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
AmericInn by Wyndham Monroe

AmericInn by Wyndham Monroe

2.5 out of 5
424 4th Ave, Monroe, WI
Free Cancellation
Reserve now, pay when you stay
$121 nightly
The price is $132 total per night
$132 total
Oct 27 - Oct 28
Total with taxes and fees
This hotel features an indoor pool and a hot tub. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Hot Tub
Hampton Inn Freeport

Hampton Inn Freeport

2.5 out of 5
109 S Galena Ave, Freeport, IL
$106 nightly
The price is $117 total per night
$117 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free perks like buffet breakfast and free self parking. A business center, free WiFi in public areas, and dry cleaning are also on offer.
Pool
Breakfast included
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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 are vacation packages to Winslow?
Travelocity has flight and hotel packages from an incredible $325. With these kinds of savings, you'll be saying hello to Winslow before long.
Where can I get the best vacation package deals for Winslow?
It's hard to look past Travelocity when it comes to piecing together your Winslow package deal. There are as many as 400 partner airlines and 1,000,000 properties worldwide to select from. Secure your trip now and get ready to cross another exciting destination off your bucket list.
Why should I purchase my Winslow vacation bundle with Travelocity?
Savings, support and a stress-free booking are just the beginning. Enjoy a fulfilling travel experience knowing you can rely on our expert team of customer support professionals 24/7. With the Travelocity Price Match Guarantee, you know you're getting the best deal available.
Can I save money on my Winslow car rental if I book it with my hotel or flight?
You sure can — combine your car, flight and hotel into a Winslow vacation package and you can save tons. With so much to see in and around Winslow, having your own wheels will make exploring easy. Once you're in the driver's seat, turn up the tunes and cruise toward Wrigley Field, a renowned attraction roughly 120 mi from Winslow.
Which airport is best for Winslow?
Many travelers choose to fly into Dane County Regional Airport (MSN), 50 mi northeast of downtown Winslow. Others prefer Rockford, IL (RFD-Greater Rockford) (40 mi away from central Winslow) or Dubuque Regional Airport (DBQ) (45 mi away from central Winslow).

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