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Winthrop Harbor

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Cheap Flights to Winthrop Harbor

Fall in love at first flight with your vacation to Winthrop Harbor by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Winthrop Harbor on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Winthrop Harbor, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Winthrop Harbor

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winthrop Harbor with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the ORD airport.

What is the cheapest month to fly to Winthrop Harbor?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Winthrop Harbor are in , but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winthrop Harbor?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find  to choose from for your flight to Winthrop Harbor.

What airport is best to fly into Winthrop Harbor?

When you’re planning your trip to Winthrop Harbor, convenience is the name of the game. Luckily, Winthrop Harbor Kenosha Regional Airport is nearby so you can deplane and get going on checking off everything on your Winthrop Harbor must-do list.

How much are flights to Winthrop Harbor?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winthrop Harbor on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as , you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Winthrop Harbor?

The trick to saving a stack of cash on your flight to Winthrop Harbor? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as  right now, why wait?

Winthrop Harbor Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$440

Last Minute Hotel Deals in Winthrop Harbor

LA VILLA MOTEL

LA VILLA MOTEL

2 out of 5
1401 Sheridan Rd Winthrop Harbor IL
Stay at this motel in Winthrop Harbor. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Elizabeth Park and Beulah Park are located ...
6.6/10 (67 reviews)
Good service

Reviewed on Sep 30, 2025

LA VILLA MOTEL
Motel Sun Inn

Motel Sun Inn

2.5 out of 5
301 Sheridan Road Winthrop Harbor IL
Stay at this motel in Winthrop Harbor. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Spring Bluff Forest Preserve and North Point ...
6.8/10 (275 reviews)
I have stayed here several times in the last year and a half. The room is very clean! Staff is very kind and helpful! Good rate! Thank you again for everything!

Reviewed on Nov 11, 2025

Motel Sun Inn
La Quinta Inn & Suites by Wyndham Chicago Gurnee

La Quinta Inn & Suites by Wyndham Chicago Gurnee

3 out of 5
5688 Northridge Rd Gurnee IL
Book a stay at this business-friendly hotel in Gurnee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7.8/10 Good! (1,418 reviews)
STAY HERE. AMAZING ROOMS!

Reviewed on Nov 18, 2025

La Quinta Inn & Suites by Wyndham Chicago Gurnee
Days Inn by Wyndham Pleasant Prairie Kenosha

Days Inn by Wyndham Pleasant Prairie Kenosha

2.5 out of 5
7540 118th Ave Pleasant Prairie WI
Book a stay at this business-friendly hotel in Pleasant Prairie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
8.4/10 Very Good! (334 reviews)
Both Dimitri & Bella were very accommodating. Just ask if you need something and they will do what they can—with a smile. Thanks!

Reviewed on Nov 21, 2025

Days Inn by Wyndham Pleasant Prairie Kenosha
Hotel Indigo Chicago-Vernon Hills by IHG

Hotel Indigo Chicago-Vernon Hills by IHG

3.5 out of 5
450 N Milwaukee Ave Vernon Hills IL
Book a stay at this boutique hotel in Vernon Hills. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (1,004 reviews)
Only thing I didn’t like was there was no microwave in the room. But the staff was amazing!

Reviewed on Nov 10, 2025

Hotel Indigo Chicago-Vernon Hills by IHG
DoubleTree by Hilton Libertyville - Mundelein

DoubleTree by Hilton Libertyville - Mundelein

4 out of 5
510 E IL Route 83 Mundelein IL
Book a stay at this business-friendly hotel in Mundelein. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.4/10 Very Good! (1,003 reviews)
Room was clean and the staff was friendly.

Reviewed on Nov 17, 2025

DoubleTree by Hilton Libertyville - Mundelein
Sonesta ES Suites Chicago Waukegan Gurnee

Sonesta ES Suites Chicago Waukegan Gurnee

3 out of 5
1440 S White Oak Dr Waukegan IL
Book a stay at this business-friendly hotel in Waukegan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,528 reviews)
Had a great stay great hospitality

Reviewed on Nov 16, 2025

Sonesta ES Suites Chicago Waukegan Gurnee
Comfort Suites Grayslake near Libertyville North

Comfort Suites Grayslake near Libertyville North

2.5 out of 5
1775 East Belvidere Road Grayslake IL
Book a stay at this business-friendly hotel in Grayslake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,001 reviews)
My stay at the Comfort Suites was comfortable and quiet, with the room and pool area being very clean. I also appreciated the friendly cleaning staff who greeted guests in the hallway. As my room faced the east, there was a beautiful sunrise from my window! Great stay for the price!

Reviewed on Nov 22, 2025

Comfort Suites Grayslake near Libertyville North
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.