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Winnetka Flights as Low as $61
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Cheap Flights to Winnetka
Fall in love at first flight with your vacation to Winnetka 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 Winnetka on Hotwire, and you’ll be up, up, and on a getaway in no time.
Because once the wheels are down in Winnetka, the good times start rolling. So buckle up, you’re in for a fun ride.
Frequently Asked Questions About flights to Winnetka
Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winnetka 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 CHI airport.
What is the cheapest month to fly to Winnetka?
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 Winnetka are in May, but when you book your flight on Hotwire, savings are always in season.
How many airlines fly to Winnetka?
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 Winnetka.
What airport is best to fly into Winnetka?
When you’re planning your trip to Winnetka, convenience is the name of the game. Luckily, Winnetka Chicago Executive Airport is nearby so you can deplane and get going on checking off everything on your Winnetka must-do list.
How much are flights to Winnetka?
Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winnetka on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $61, 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 Winnetka?
The trick to saving a stack of cash on your flight to Winnetka? 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 $61 right now, why wait?
Destination airport | O'Hare Intl. |
|---|---|
Destination airport IATA code | ORD |
Roundtrip price | $64 |
Last Minute Hotel Deals in Winnetka
Congress Plaza Hotel
We mainly go to Chicago for medical appointments and it is *so awesome* that you can actually open the windows here.That is the main reason we chose it. Because Dad has cancer we aired it out and then ran our own air purifier. No bad smells or anything, we're just being cautious because of his health. ...
Reviewed on Feb 27, 2026
Hotel Riu Plaza Chicago
Good job
Reviewed on Feb 27, 2026
Embassy Suites by Hilton Chicago Downtown River North
Room was clean, beds weren't that comfortable. Other, than that I would stay there again.
Reviewed on Feb 27, 2026
Hilton Chicago/Magnificent Mile Suites
The room was so nice and well laid out. The beds were the most comfortable I’ve ever slept on. Great location. Expensive parking though.
Reviewed on Feb 27, 2026
Eurostars Magnificent Mile
Room was gorgeous, felt very luxurious for the price! Front desk staff was great at check out!
Reviewed on Feb 26, 2026
Hilton Chicago
Very good!
Reviewed on Feb 27, 2026
Aloft Chicago Mag Mile
Great!
Reviewed on Feb 27, 2026
Hyatt Regency Chicago
The room was spotless. The front desk helped make sure my reservation was taken care of despite travel delays outside of my control. Highly recommended this property and their staff
Reviewed on Feb 24, 2026
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