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Winthrop Harbor

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Winthrop Harbor Flights as Low as $74

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 May, 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 14 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 $74, 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 $74 right now, why wait?

Winthrop Harbor Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$74

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! (1,001 reviews)
SO GLAD I HAD MY WATER SHOES!!

Reviewed on Mar 9, 2026

Great Wolf Lodge Illinois
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! (488 reviews)
Room was clean. Staff friendly

Reviewed on Mar 12, 2026

Days Inn by Wyndham Sturtevant / Racine / Mount Pleasant
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! (1,003 reviews)
Breakfast had many options to choose from, even had chocolate waffle batter along with the regular batter. The hotel room was an average type room. The fan in the bathroom didn't work, it sounded like it was going to fall off the ceiling. We didn't use the pool/hot tub, as you needed to ask the front ...

Reviewed on Mar 14, 2026

Best Western Executive Inn Kenosha/Pleasant Prairie
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 ...
8.8/10 Excellent! (78 reviews)
Very nice

Reviewed on Mar 14, 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! (1,003 reviews)
This was a quick one night stay. We arrived quite late and the gentleman at the counter was very descriptive as to where to go as well as how to keep the “old school magnetic” key to work. Implying that it couldn’t be anywhere near a cellphone. I totally get it but it didn’t require a 45 second explanation ...

Reviewed on Mar 14, 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! (1,543 reviews)
The room was pretty clean and the staff were helpful during my stay

Reviewed on Mar 13, 2026

La Quinta Inn & Suites by Wyndham Chicago Gurnee
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 ...
8.6/10 Excellent! (1,002 reviews)
Clean room, locate

Reviewed on Mar 7, 2026

DoubleTree by Hilton Libertyville - Mundelein
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)
Our stay was great. Free breakfast for guests. I loved that they served breakfast earlier due to the Navy boot camp graduation. The only complaint would be The gym room has old equipment and smells like old sweat. But that would not stop me from booking again if visiting the area.

Reviewed on Mar 14, 2026

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.