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.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $552, price is now $390 per person
$390
per person
Jan 22 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $910, price is now $574 per person
$574
per person
Jan 23 - Jan 27
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) 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.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $851, price is now $578 per person
$578
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This smoke-free hotel includes 3 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $704, price is now $483 per person
$483
per person
Jan 28 - Jan 31
found 18 hours 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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $864, price is now $594 per person
$594
per person
Dec 18 - Dec 22
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.

Top Winslow hotels deals

Eugene Hotel

Eugene Hotel

2 out of 5
1517 11th St Monroe WI
Free Cancellation
Reserve now, pay when you stay
$100 nightly
The price is $110 total per night
$110 total
Nov 15 - Nov 16
Total with taxes and fees
A 24-hour gym is featured at this hotel, along with free self parking. WiFi in public areas is free. A fireplace in the lobby and express check-in are also provided.
Pet friendly
Parking included
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 $114 total per night
$114 total
Nov 22 - Nov 23
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
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
Dec 7 - Dec 8
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
Country Inn & Suites by Radisson, Stockton, IL

Country Inn & Suites by Radisson, Stockton, IL

2.5 out of 5
200 Dillon Ave Stockton IL
$69 nightly
The price is $76 total per night
$76 total
Nov 29 - Nov 30
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
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
$93 nightly
The price is $103 total per night
$103 total
Nov 15 - Nov 16
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
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
$98 nightly
The price is $108 total per night
$108 total
Nov 22 - Nov 23
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
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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 $390. 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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