Search Cheap Flights to
Winthrop Harbor

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Winthrop Harbor Flights as Low as $83

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

Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Frontier Airlines
Bargain Flight
Frontier Airlines
American Airlines
Delta
JetBlue Airways
Frontier Airlines
Delta
Frontier Airlines
Contour Airlines
Alaska Airlines
Sun Country Airlines

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 January, 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 15 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 Chicago Executive 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 $83, 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 $83 right now, why wait?

Winthrop Harbor Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$83

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 (90 reviews)
"It was exactly what I was expecting. As long as you aren’t high maintenance, it’s a fine inexpensive stay 20 from the navy base."

Reviewed on Nov 8, 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 ...
7/10 Good! (301 reviews)
"The room and bathroom light both turned on frequently during the night. The entire motel needs an upgrade. I did see some plastic up perhaps they are doing renovations. The building reeks of moth balls which was not a great sign and though I did not encounter bedbugs the sheets were stained from ..."

Reviewed on Nov 7, 2026

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 ...
8/10 Very Good! (1,877 reviews)
"For the price I paid, the hotel was very good. We came for the hot tub, and it didn't disappoint. Temperature was perfect, and it was very clean. Room was a bit small, but we were only there 1 night. Breakfast was excellent. Many items to choose from. My only complaint was the breakfast worker wasn't ..."

Reviewed on Nov 10, 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 ...
DoubleTree by Hilton Libertyville - Mundelein
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. ...
8.4/10 Very Good! (1,006 reviews)
"Checking in was a mess but other than that we had a great time."

Reviewed on Nov 8, 2026

Great Wolf Lodge Illinois
The Inn on Sheridan

The Inn on Sheridan

3.5 out of 5
2723 Sheridan Rd Zion IL
Book a stay at this business-friendly hotel in Zion. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
The Inn on Sheridan
Motel 6 Libertyville, IL

Motel 6 Libertyville, IL

2 out of 5
1809 N Milwaukee Ave Libertyville IL
Book a stay at this business-friendly motel in Libertyville. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in ...
Motel 6 Libertyville, IL
Courtyard Chicago Waukegan Gurnee

Courtyard Chicago Waukegan Gurnee

3 out of 5
3800 Northpoint Blvd Waukegan IL
Book a stay at this business-friendly hotel in Waukegan. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
Courtyard Chicago Waukegan Gurnee
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.