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Winthrop Harbor

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Winthrop Harbor Flights as Low as $98

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

Frontier Airlines
Tue, Sep 29 - Tue, Oct 6
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$98 Roundtrip, found 4 days ago
$98
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Sep 29 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Oct 6, priced at $98 found 4 days ago
Frontier Airlines
Mon, Aug 10 - Mon, Aug 17
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$108 Roundtrip, found 5 days ago
$108
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Aug 10 from George Bush Intercontinental to O'Hare Intl., returning Mon, Aug 17, priced at $108 found 5 days ago
Frontier Airlines
Sat, Jul 4 - Tue, Jul 21
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$111 Roundtrip, found 5 days ago
$111
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Jul 4 from George Bush Intercontinental to O'Hare Intl., returning Tue, Jul 21, priced at $111 found 5 days ago
Frontier Airlines
Sat, Aug 1 - Fri, Aug 14
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$113 Roundtrip, found 5 days ago
$113
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Aug 1 from George Bush Intercontinental to O'Hare Intl., returning Fri, Aug 14, priced at $113 found 5 days ago
Frontier Airlines
Fri, Aug 14 - Thu, Aug 20
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 3 days ago
$118
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Fri, Aug 14 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Thu, Aug 20, priced at $118 found 3 days ago
Frontier Airlines
Wed, Sep 16 - Tue, Sep 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$148 Roundtrip, found 9 hours ago
$148
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Wed, Sep 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 29, priced at $148 found 9 hours ago
Bargain Flight
Fri, Aug 21 - Sun, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$175 Roundtrip, found 1 day ago
$175
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Fri, Aug 21 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Aug 23, priced at $175 found 1 day ago
Frontier Airlines
Fri, Aug 14 - Tue, Aug 18
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$178 Roundtrip, found 4 days ago
$178
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Aug 14 from Los Angeles Intl. to O'Hare Intl., returning Tue, Aug 18, priced at $178 found 4 days ago
American Airlines
Wed, Sep 16 - Tue, Sep 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 9 hours ago
$197
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Wed, Sep 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 29, priced at $197 found 9 hours ago
Frontier Airlines
Mon, Nov 9 - Tue, Nov 10
TPA
Tampa Intl.
ORD
O'Hare Intl.
$203 Roundtrip, found 1 day ago
$203
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Nov 9 from Tampa Intl. to O'Hare Intl., returning Tue, Nov 10, priced at $203 found 1 day ago
Delta
Wed, Sep 16 - Tue, Sep 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$207 Roundtrip, found 9 hours ago
$207
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Sep 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 29, priced at $207 found 9 hours ago
JetBlue Airways
Thu, Aug 13 - Tue, Aug 18
FLL
Fort Lauderdale - Hollywood Intl.
ORD
O'Hare Intl.
$207 Roundtrip, found 1 day ago
$207
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Aug 13 from Fort Lauderdale - Hollywood Intl. to O'Hare Intl., returning Tue, Aug 18, priced at $207 found 1 day ago
Alaska Airlines
Sat, Oct 3 - Mon, Oct 5
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$249 Roundtrip, found 5 days ago
$249
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Sat, Oct 3 from San Francisco Intl. to O'Hare Intl., returning Mon, Oct 5, priced at $249 found 5 days ago
Delta
Tue, Jul 7 - Tue, Jul 14
DAL
Love Field
ORD
O'Hare Intl.
$318 Roundtrip, found 1 day ago
$318
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 7 from Love Field to O'Hare Intl., returning Tue, Jul 14, priced at $318 found 1 day ago
Contour Airlines
Sat, Sep 12 - Sun, Sep 13
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$334 Roundtrip, found 8 hours ago
$334
Roundtrip
found 8 hours ago
Select Contour Airlines flight, departing Sat, Sep 12 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sun, Sep 13, priced at $334 found 8 hours ago
Sun Country Airlines
Thu, Aug 20 - Sun, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$353 Roundtrip, found 1 day ago
$353
Roundtrip
found 1 day ago
Select Sun Country Airlines flight, departing Thu, Aug 20 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Aug 23, priced at $353 found 1 day ago

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 September, 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 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 $98, 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 $98 right now, why wait?

Winthrop Harbor Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$108

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! (1,002 reviews)
"My kids loved the waterslides everything."

Reviewed on May 30, 2026

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Great Wolf Lodge Illinois
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! (1,005 reviews)
"There was no restaurant for dinner. There was no lobby coffee on the weekend. The shower leaked, and was not repaired on the weekend. The motel did not appear to be a successful business since all the salons were unused. I only needed 4 nights of sleep, and it was fine for that."

Reviewed on Jun 5, 2026

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DoubleTree by Hilton Libertyville - Mundelein
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! (1,010 reviews)
"Great!"

Reviewed on Jun 4, 2026

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Hotel Indigo Chicago-Vernon Hills by IHG
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 Gurnee Mills are located ...
8.2/10 Very Good! (180 reviews)
"This hotel went way above what was expected, especially for the price. If you are going to a Navy graduation, this is a very affordable option."

Reviewed on Jun 6, 2026

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Days Inn by Wyndham Waukegan
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! (1,693 reviews)
"Regarding cleanliness, there were long hairs on the shower wall. More details aside, a major security issue occurred just minutes after check-in: the receptionist accidentally assigned our room and handed a key to another guest, who then walked into our room. This was a shocking and completely unacceptable ..."

Reviewed on Jun 8, 2026

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La Quinta Inn & Suites by Wyndham Chicago Gurnee
Sonesta Simply Suites Chicago Libertyville

Sonesta Simply Suites Chicago Libertyville

2 out of 5
1100 N Us Route 45 Libertyville IL
Book a stay at this business-friendly hotel in Libertyville. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the ...
9.2/10 Wonderful! (1,011 reviews)
"The room seemed clean, there was just a an odd smoky smell that permeated the room...or.maybe pet odor? It appeared people could bring pets which is a negative for us due to my allergies. I should have called to ask. Otherwise the gal at the front desk was courteous and efficient. I thought the bed ..."

Reviewed on Jun 7, 2026

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Sonesta Simply Suites Chicago Libertyville
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! (539 reviews)
"The room and bathroom were cleaned well. However I could tell the carpeted floor wasn't clean as it smelled slightly like stinky feet and bleach ( no I didn't get down and sniff it 😆 the smell was in the air. I also found a brown pill on the floor and a Bobby pin..."

Reviewed on Jun 5, 2026

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Days Inn by Wyndham Sturtevant / Racine / Mount Pleasant
The Stella Hotel & Ballroom

The Stella Hotel & Ballroom

3.5 out of 5
5706 8th Ave Kenosha WI
Book a stay at this business-friendly hotel in Kenosha. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,012 reviews)
"Neat old building, not sure if it was originally a hotel. Modernized. Mostly clean. Couple of hair strands found on the bathroom floor. Good coffee shop."

Reviewed on Jun 4, 2026

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The Stella Hotel & Ballroom
See all 690 properties in Winthrop Harbor
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.