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Winthrop Harbor

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Winthrop Harbor Flights as Low as $111

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 July, 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 $111, 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 $111 right now, why wait?

Winthrop Harbor Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$110

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 ...
6.8/10 (72 reviews)
"Needed a last minute place to stay, and this was clean and quiet, with attentive staff, though poorly maintained (eg old furniture stored in the hallway, bathroom exhaust did not work). The room had a huge hot tub in the corner with a wall mirror. Fantastic location, easy drive to downtown Zion and ..."

Reviewed on Jun 20, 2026

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 (280 reviews)
"The staff were so nice! The rooms and bathroom were so clean. The building is a little older but everything was in good shape. Free WiFi use and the air conditioner worked perfectly. The price was also fair. It was 90 dollars and a 50 dollar deposit fee but you get the 50 dollars back in your account ..."

Reviewed on Jun 25, 2026

Motel Sun Inn
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! (1,008 reviews)
"Everything was excellent! The only issue was that we had to wait in line to use the microwave to heat our meals. If guests are expected to stay for an extended period, it would be much more convenient to have a microwave in each room, or at least easier access to one. Overall, we had a great experience, ..."

Reviewed on Jun 27, 2026

Great Wolf Lodge Illinois
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)
"The water pressure in the shower was so bad. Mine and my daughter’s hair was greasy and weighed down because we could not rinse our hair well. Told the staff that I wanted to talk to the manager and called them multiple times after check out with NO CALL BACK. Do not stay here. It’s ridiculous that ..."

Reviewed on Jun 23, 2026

Hotel Indigo Chicago-Vernon Hills by IHG
Wingate by Wyndham Gurnee

Wingate by Wyndham Gurnee

3 out of 5
6090 Gurnee Mills Blvd E Gurnee IL
Book a stay at this business-friendly hotel in Gurnee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,002 reviews)
"Nice location and clean rooms"

Reviewed on Jun 24, 2026

Wingate by Wyndham Gurnee
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 ...
8.8/10 Excellent! (1,009 reviews)
"All Good"

Reviewed on Jun 27, 2026

Best Western Executive Inn Kenosha/Pleasant Prairie
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! (1,713 reviews)
"Quiet, clean and comfortable, close to the naval base, very convenient., tge 2 beds bedrooms did help a lot"

Reviewed on Jun 27, 2026

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 family-friendly hotel in Pleasant Prairie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
8.2/10 Very Good! (487 reviews)
"Clean room. Great service."

Reviewed on Jun 28, 2026

Days Inn by Wyndham Pleasant Prairie Kenosha
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.