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Winthrop Harbor

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Winthrop Harbor Flights as Low as $63

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

Spirit Airlines
Tue, Aug 5 - Wed, Aug 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, found 2 days ago
$63
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Aug 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Aug 6, priced at $63 found 2 days ago
Spirit Airlines
Sat, Sep 27 - Tue, Sep 30
LGA
LaGuardia
ORD
O'Hare Intl.
$90 Roundtrip, found 3 hours ago
$90
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sat, Sep 27 from LaGuardia to O'Hare Intl., returning Tue, Sep 30, priced at $90 found 3 hours ago
United
Fri, Sep 19 - Wed, Sep 24
LGA
LaGuardia
ORD
O'Hare Intl.
$98 Roundtrip, found 4 days ago
$98
Roundtrip
found 4 days ago
Select United flight, departing Fri, Sep 19 from LaGuardia to O'Hare Intl., returning Wed, Sep 24, priced at $98 found 4 days ago
Frontier Airlines
Mon, Jul 28 - Sat, Aug 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 3 hours ago
$100
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Mon, Jul 28 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 2, priced at $100 found 3 hours ago
Spirit Airlines
Tue, Sep 2 - Thu, Sep 4
MIA
Miami Intl.
ORD
O'Hare Intl.
$119 Roundtrip, just found
$119
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Sep 2 from Miami Intl. to O'Hare Intl., returning Thu, Sep 4, priced at $119 just found
Spirit Airlines
Wed, Sep 24 - Sat, Sep 27
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$130 Roundtrip, found 1 hour ago
$130
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, Sep 24 from Los Angeles Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $130 found 1 hour ago
American Airlines
Sat, Aug 16 - Sat, Aug 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 12 hours ago
$132
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Sat, Aug 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 16, priced at $132 found 12 hours ago
Frontier Airlines
Thu, Sep 4 - Mon, Sep 8
PHL
Philadelphia Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 7 hours ago
$138
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Thu, Sep 4 from Philadelphia Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $138 found 7 hours ago
Delta
Tue, Aug 5 - Tue, Aug 12
LGA
LaGuardia
ORD
O'Hare Intl.
$139 Roundtrip, found 3 days ago
$139
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Aug 5 from LaGuardia to O'Hare Intl., returning Tue, Aug 12, priced at $139 found 3 days ago
JetBlue Airways
Tue, Sep 2 - Wed, Sep 10
PHL
Philadelphia Intl.
ORD
O'Hare Intl.
$203 Roundtrip, found 7 hours ago
$203
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Tue, Sep 2 from Philadelphia Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $203 found 7 hours ago
Alaska Airlines
Sat, Nov 15 - Wed, Nov 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 1 hour ago
$216
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Sat, Nov 15 from Los Angeles Intl. to O'Hare Intl., returning Wed, Nov 19, priced at $216 found 1 hour ago
Frontier Airlines
Tue, Jul 22 - Tue, Jul 29
TTN
Mercer
ORD
O'Hare Intl.
$264 Roundtrip, found 1 day ago
$264
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jul 22 from Mercer to O'Hare Intl., returning Tue, Jul 29, priced at $264 found 1 day ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Tue, Dec 23 - Tue, Dec 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$325 Roundtrip, found 13 hours ago
$325
Roundtrip
found 13 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Tue, Dec 23 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 30, priced at $325 found 13 hours ago
Icelandair
Fri, Oct 3 - Wed, Oct 8
IST
Istanbul
ORD
O'Hare Intl.
$598 Roundtrip, found 2 days ago
$598
Roundtrip
found 2 days ago
Select Icelandair flight, departing Fri, Oct 3 from Istanbul to O'Hare Intl., returning Wed, Oct 8, priced at $598 found 2 days ago
Accessrail
Tue, Sep 2 - Thu, Sep 4
AVT
Aventura Brightline Train Station
ORD
O'Hare Intl.
$855 Roundtrip, just found
$855
Roundtrip
just found
Select Accessrail flight, departing Tue, Sep 2 from Aventura Brightline Train Station to O'Hare Intl., returning Thu, Sep 4, priced at $855 just found
Accessrail
Tue, Sep 2 - Thu, Sep 4
EKW
Miami Central Brightline Train Station
ORD
O'Hare Intl.
$855 Roundtrip, just found
$855
Roundtrip
just found
Select Accessrail flight, departing Tue, Sep 2 from Miami Central Brightline Train Station to O'Hare Intl., returning Thu, Sep 4, priced at $855 just found

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 August, 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 $63, 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 $63 right now, why wait?

Winthrop Harbor Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$63

Last Minute Hotel Deals in Winthrop Harbor

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 ...
6.6/10 (227 reviews)
"The location was ideal for going to the beach. The beach was perfect. The hotel is run down but the room was clean, the shower was amazing and the AC was great. The check in was definitely concerning when you arrive you have to dial a phone outside a window with posters warning of the surveillance, ..."

Reviewed on Jul 9, 2025

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Motel Sun Inn
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 ...
6.2/10 (36 reviews)
"Nice"

Reviewed on Jul 8, 2025

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LA VILLA MOTEL
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
Stay at this 3-star business-friendly hotel in Gurnee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7.8/10 Good! (1,241 reviews)
"Friendly"

Reviewed on Jul 12, 2025

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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
Stay at this 4-star business-friendly hotel in Mundelein. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.4/10 Very Good! (1,003 reviews)
"Old, need to be updated, bathrooms not bad. We’re very clean. Carpet and Decor need to be undated."

Reviewed on Jul 9, 2025

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DoubleTree by Hilton Libertyville - Mundelein
Great Wolf Lodge Illinois
Great Wolf Lodge Illinois
3 out of 5
1700 Nations Dr, Gurnee, IL
Stay at this 3-star 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)
"I loved this place as a little weekend getaway with the kiddos. Pros: registration was easy, parking was easy, the wolf ears are adorable, fun free activities for the kids in the lobby, food options in the resort so you don’t have to leave. Cons: 20 dollar parking per night per car. With rates this ..."

Reviewed on Jul 12, 2025

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Great Wolf Lodge Illinois
Wingate by Wyndham Gurnee
Wingate by Wyndham Gurnee
2.5 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 ...
8.8/10 Excellent! (1,007 reviews)
"Great stay!! Staff was friendly & helpful. The room was clean & comfy. No complaints"

Reviewed on Jul 12, 2025

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Wingate by Wyndham Gurnee
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
Stay at this 3.5-star 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! (1,019 reviews)
"We were on the 6th floor so it was quiet. I don’t think I could say that for any other floor due to there was a lacrosse tournament in the area and I saw lots of kids when going to the lobby. Our room was clean and large. Hotel is just older. Areas have been updated but still overall condition is ..."

Reviewed on Jul 13, 2025

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Hotel Indigo Chicago-Vernon Hills by IHG
Motel 6 Libertyville, IL
Motel 6 Libertyville, IL
2 out of 5
1809 N Milwaukee Ave, 94 Exit Buckly Rd HWY137, Libertyville, IL
Stay at this motel in Libertyville. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
6.6/10 (998 reviews)
"a cozy night in North Chicago"

Reviewed on Jul 13, 2025

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Motel 6 Libertyville, IL
See all 602 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.