Winslow Holidays from £955
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Your Winslow Holiday
Memorable adventures await when you reserve a holiday package to Winslow. Whether you're a foodie, history buff or just a traveller who loves to discover new places, there's something for everyone in this awesome city. Any trip to Winslow has to include a little sightseeing. Lake Le Aqua Na State Park is a great place to begin exploring. Stop daydreaming and start travelling. Check out the range of options on Expedia today and put your Winslow holiday plans into motion!
Top Winslow Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was £1,123, price is now £955 per person
£955
per person
1 Jul - 5 Jul
found 8 hours ago
Return flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (2,707 reviews)
The staff at Hotel Felix were kind, thoughtful, and genuinely helpful throughout my stay. The location is also a strong point — walking distance to a lot of great Chicago spots, which made getting around easy.
My experience was somewhat diminished by the mandatory Urban Fee added at check-in. I understand many hotels are moving in this direction, but travelers should be aware of the additional required cost when budgeting for their stay. Outside of that, the team and location were the highlights for me.
Reviewed on 12 May 2026
Swissotel - Chicago
Downtown Chicago
Price was £1,238, price is now £991 per person
£991
per person
1 Jul - 5 Jul
found 8 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
This property has a great location. The hotel was really clean! We enjoyed the bar atmosphere, and we had a delicious appetizer! I will highly recommend this location for a great getaway for couples! Page at the front desk and Prudencia in housekeeping were amazing!
Reviewed on 13 May 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £1,242, price is now £1,041 per person
£1,041
per person
1 Jul - 5 Jul
found 8 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
Great location.
Very friendly and helpful staff.
Reviewed on 13 May 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was £1,164, price is now £981 per person
£981
per person
1 Jul - 5 Jul
found 8 hours ago
Return flight included
London (LON) to Chicago (ORD)
8.8/10 Excellent! (2,148 reviews)
Staff was very good, attentive. The property itself is in a great location, but the room showed some wear and tear - exposed drywall screws holding on bathroom door trim with some paint slapped on it, smelly sink, water damage and peeling paint on inside window sill, visually boring interior that looks like it's from the 1990's
Reviewed on 12 May 2026
Winslow Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Lake Le Aqua Na State Park, Famous Fossil Winery and Stagecoach Golf Course |
Top hotels in Winslow
Country Inn & Suites by Radisson, Freeport, IL
1710 South Dirck Drive Freeport IL
Fully refundable
The price is £101 per night from 17 May to 18 May
£101
17 May - 18 May
includes taxes & fees
9/10 Wonderful! (893 reviews)
Worked perfect for me
Reviewed on 28 Apr 2026
Super 8 by Wyndham Monroe WI
500 6th St and Hwy 69 Monroe WI
Fully refundableReserve now, pay when you stay
The price is £63 per night from 21 May to 22 May
£63
21 May - 22 May
includes taxes & fees
9/10 Wonderful! (856 reviews)
Best staff in the world! So accommodating, professional, and kind.
Reviewed on 6 May 2026
Hampton Inn Freeport
109 S Galena Ave Freeport IL
Fully refundableReserve now, pay when you stay
The price is £93 per night from 26 May to 27 May
£93
26 May - 27 May
includes taxes & fees
8.8/10 Excellent! (473 reviews)
Room was clean, staff was nice, breakfast was fresh and tasty!
Reviewed on 4 May 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
