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Winthrop Harbor

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Winthrop Harbor Flights as Low as $59

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

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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 April, 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 16 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 $59, 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 $59 right now, why wait?

Winthrop Harbor Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$58

Last Minute Hotel Deals in Winthrop Harbor

Great Wolf Lodge Illinois

Great Wolf Lodge Illinois

3 out of 5
1700 Nations Dr Gurnee IL
Book a stay at this family-friendly resort in Gurnee. Enjoy 6 indoor pools, 5 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (1,011 reviews)
Family of four, girls are 9 and 14. We go to different great wolf lodges. This one wasnt bad, two attractions were closed temporarily due to kids puking. Be present with your kids, go on the water slides, tube the lazy river, get smoked by big waves in the wave pool. Sad seeing all the parents on ...

Reviewed on Apr 4, 2026

Great Wolf Lodge Illinois
Best Western Executive Inn Kenosha/Pleasant Prairie

Best Western Executive Inn Kenosha/Pleasant Prairie

2.5 out of 5
7220 122nd Ave Kenosha WI
Book a stay at this business-friendly hotel in Kenosha. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,006 reviews)
Great people. Comfy bed. Nice HOT hot tub. Great breakfast.

Reviewed on Apr 5, 2026

Best Western Executive Inn Kenosha/Pleasant Prairie
Days Inn by Wyndham Sturtevant / Racine / Mount Pleasant

Days Inn by Wyndham Sturtevant / Racine / Mount Pleasant

2 out of 5
13340 Hospitality Ct Mount Pleasant WI
Book a stay at this business-friendly hotel in Mount Pleasant. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
8.2/10 Very Good! (503 reviews)
Everything was nice

Reviewed on Mar 31, 2026

Days Inn by Wyndham Sturtevant / Racine / Mount Pleasant
Days Inn by Wyndham Waukegan

Days Inn by Wyndham Waukegan

2 out of 5
630 N Green Bay Road Waukegan IL
Stay at this motel in Waukegan. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Six Flags Great America and The People's Choice Family ...
8.6/10 Excellent! (101 reviews)
Excellent

Reviewed on Apr 5, 2026

Days Inn by Wyndham Waukegan
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 ...
8.4/10 Very Good! (1,002 reviews)
Our experience at the hotel was extremely distressing and unacceptable. We felt so unsafe on the property that we did not stay in the room for more than 30 seconds before leaving. As I was entering the building, an individual approached a very tall Black man and, completely unprovoked, used a racial ...

Reviewed on Apr 4, 2026

Hotel Indigo Chicago-Vernon Hills by IHG
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 ...
8/10 Very Good! (1,585 reviews)
hot tub was great chlorine smell burned our eyes. breakfast was great though no notes solid stay

Reviewed on Apr 5, 2026

La Quinta Inn & Suites by Wyndham Chicago 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! (1,005 reviews)
Well maintained

Reviewed on Apr 5, 2026

Comfort Suites Grayslake near Libertyville North
Country Inn & Suites by Radisson Kenosha - Pleasant Prairie

Country Inn & Suites by Radisson Kenosha - Pleasant Prairie

2.5 out of 5
7011 122nd Ave Kenosha WI
Book a stay at this business-friendly hotel in Kenosha. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,003 reviews)
My stay here was unbearable, but it mostly had to do with the other clientele. I think it’s very sad that if you choose an affordable hotel, you can pretty much guarantee that the least respectful people imaginable will also be there. They had just experienced a major plumbing catastrophe which I ...

Reviewed on Apr 5, 2026

Country Inn & Suites by Radisson Kenosha - Pleasant Prairie
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.