Deals on vacations and trips to Winslow

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Winslow flight + hotel vacation packages

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Holiday Inn Club Vacations at Lake Geneva Resort by IHG

Holiday Inn Club Vacations at Lake Geneva Resort by IHG

3.5 out of 5
Price was $489, price is now $343 per person
$343
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This smoke-free resort features a golf course, a full-service spa, and a water park. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy a meal in one of the 4 restaurants and free perks like free self parking and an area shuttle.
Destination Geneva National

Destination Geneva National

4 out of 5
Save 100% on your flight
Price was $588, price is now $388 per person
$388
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
A golf course, 5 restaurants, and an indoor pool are all featured at this smoke-free hotel. Relax with a drink at one of the 4 bars/lounges and enjoy perks like free self parking. You'll appreciate the gym, poolside bar, and snack bar/deli.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,355, price is now $906 per person
$906
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip flight included
Dallas (DAL) 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,295, price is now $900 per person
$900
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
This hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.
Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

4 out of 5
Save 100% on your flight
Price was $724, price is now $510 per person
$510
per person
Nov 13 - Nov 15
found 14 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This smoke-free resort features a golf course, a full-service spa, and a water park. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy downhill skiing. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities.

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
$110 nightly
The price is $122 total per night
$122 total
Sep 27 - Sep 28
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
City Express By Marriott Freeport

City Express By Marriott Freeport

3 out of 5
1060 Riverside Dr Freeport IL
Free Cancellation
Reserve now, pay when you stay
$107 nightly
The price is $119 total per night
$119 total
Sep 20 - Sep 21
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
Eugene Hotel

Eugene Hotel

2 out of 5
1517 11th St Monroe WI
Free Cancellation
Reserve now, pay when you stay
$117 nightly
The price is $128 total per night
$128 total
Sep 21 - Sep 22
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A fireplace in the lobby and express check-in are also provided.
Pet friendly
Parking included
Super 8 by Wyndham Freeport

Super 8 by Wyndham Freeport

2 out of 5
1551 Sleezer Home Rd Freeport IL
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $99 total per night
$99 total
Sep 14 - Sep 15
Total with taxes and fees
A gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. There's a safe deposit box and multilingual staff can provide around-the-clock assistance.
Breakfast included
Pet friendly
Super 8 by Wyndham Monroe WI

Super 8 by Wyndham Monroe WI

2 out of 5
500 6th St and Hwy 69 Monroe WI
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $93 total per night
$93 total
Sep 21 - Sep 22
Total with taxes and fees
This motel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
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
$76 nightly
The price is $84 total per night
$84 total
Oct 4 - Oct 5
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
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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 $343. 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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