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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $232, price is now $115 per person
$115
per person
Jan 30 - Feb 1
found 1 day 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 smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Limo/town car service, WiFi in public areas, and express check-out are also on offer.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $268, price is now $133 per person
$133
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was $676, price is now $341 per person
$341
per person
Feb 18 - Feb 22
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $355, price is now $184 per person
$184
per person
Feb 20 - Feb 22
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $393, price is now $206 per person
$206
per person
Jan 23 - Jan 26
found 1 day 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 hotel. Families will appreciate the onsite laundry facilities and in-room childcare. Relax with a drink at one of the 2 bars/lounges and get 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
$103 nightly
The price is $115 total per night
$115 total
Dec 29 - Dec 30
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
$78 nightly
The price is $86 total per night
$86 total
Nov 30 - Dec 1
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
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
$112 nightly
The price is $123 total per night
$123 total
Dec 7 - Dec 8
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
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
$81 nightly
The price is $90 total per night
$90 total
Dec 7 - Dec 8
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 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
$68 nightly
The price is $74 total per night
$74 total
Dec 4 - Dec 5
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
Darlington Inn

Darlington Inn

2 out of 5
201 Christiensen Dr Darlington WI
Free Cancellation
Reserve now, pay when you stay
$80 nightly
The price is $88 total per night
$88 total
Nov 30 - Dec 1
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
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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 $115. 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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