Deals on vacations and trips to Winslow

Save when you book Winslow package deals

Choose two or more items and save on your trip:

Winslow flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,068, price is now $703 per person
$703
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,463, price is now $912 per person
$912
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $3,349, price is now $2,117 per person
$2,117
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the 24-hour gym, bar/lounge, and laundry facilities.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,396, price is now $901 per person
$901
per person
Aug 18 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,352, price is now $889 per person
$889
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

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
Aug 2 - Aug 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
$88 nightly
The price is $98 total per night
$98 total
Aug 11 - Aug 12
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
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
$83 nightly
The price is $91 total per night
$91 total
Aug 9 - Aug 10
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
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
Jul 23 - Jul 24
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
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
Jul 19 - Jul 20
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
Hampton Inn Freeport

Hampton Inn Freeport

2.5 out of 5
109 S Galena Ave Freeport IL
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $122 total per night
$122 total
Jul 26 - Jul 27
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Winslow
View all properties
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 $703. 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).

Photos of local treasures

Browse Winslow vacation photos for more inspiration