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Winnetka

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Winnetka Flights as Low as $43

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

Frontier Airlines
Tue, Feb 4 - Tue, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$43 Roundtrip, found 15 hours ago
$43
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Tue, Feb 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Feb 4, priced at $43 found 15 hours ago
Frontier Airlines
Tue, Feb 18 - Tue, Feb 25
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$49 Roundtrip, found 1 day ago
$49
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Feb 18 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Feb 25, priced at $49 found 1 day ago
Frontier Airlines
Wed, Mar 5 - Wed, Mar 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$50 Roundtrip, found 1 day ago
$50
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Mar 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 5, priced at $50 found 1 day ago
Frontier Airlines
Wed, Feb 12 - Sat, Feb 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$55 Roundtrip, found 8 hours ago
$55
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, Feb 12 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Feb 15, priced at $55 found 8 hours ago
Frontier Airlines
Wed, Feb 12 - Wed, Feb 19
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$83 Roundtrip, found 3 hours ago
$83
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Feb 12 from Sky Harbor Intl. to O'Hare Intl., returning Wed, Feb 19, priced at $83 found 3 hours ago
Spirit Airlines
Tue, Dec 17 - Tue, Dec 17
LGA
LaGuardia
ORD
O'Hare Intl.
$98 Roundtrip, found 5 days ago
$98
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Tue, Dec 17 from LaGuardia to O'Hare Intl., returning Tue, Dec 17, priced at $98 found 5 days ago
Spirit Airlines
Tue, Dec 10 - Tue, Dec 17
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$114 Roundtrip, found 1 day ago
$114
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Dec 10 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Dec 17, priced at $114 found 1 day ago
Frontier Airlines
Mon, Dec 16 - Tue, Dec 17
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$119 Roundtrip, found 1 day ago
$119
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Dec 16 from Sky Harbor Intl. to Midway Intl., returning Tue, Dec 17, priced at $119 found 1 day ago
Delta
Tue, Feb 4 - Tue, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 15 hours ago
$132
Roundtrip
found 15 hours ago
Select Delta flight, departing Tue, Feb 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Feb 4, priced at $132 found 15 hours ago
American Airlines
Tue, Mar 4 - Tue, Mar 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 11 hours ago
$132
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Mar 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Mar 4, priced at $132 found 11 hours ago
United
Fri, Jan 17 - Mon, Jan 20
LGA
LaGuardia
ORD
O'Hare Intl.
$132 Roundtrip, found 18 hours ago
$132
Roundtrip
found 18 hours ago
Select United flight, departing Fri, Jan 17 from LaGuardia to O'Hare Intl., returning Mon, Jan 20, priced at $132 found 18 hours ago
Delta
Sun, Dec 29 - Fri, Jan 3
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$208 Roundtrip, found 1 hour ago
$208
Roundtrip
found 1 hour ago
Select Delta flight, departing Sun, Dec 29 from Newark Liberty Intl. Airport to Midway Intl., returning Fri, Jan 3, priced at $208 found 1 hour ago
JetBlue Airways
Tue, Mar 4 - Tue, Mar 4
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$232 Roundtrip, found 11 hours ago
$232
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Tue, Mar 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Mar 4, priced at $232 found 11 hours ago
Frontier Airlines
Sat, Dec 7 - Mon, Dec 9
LGA
LaGuardia
MDW
Midway Intl.
$238 Roundtrip, found 1 day ago
$238
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Dec 7 from LaGuardia to Midway Intl., returning Mon, Dec 9, priced at $238 found 1 day ago
Alaska Airlines
Wed, Mar 5 - Tue, Mar 11
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$299 Roundtrip, found 1 day ago
$299
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Wed, Mar 5 from Sky Harbor Intl. to O'Hare Intl., returning Tue, Mar 11, priced at $299 found 1 day ago
Sun Country Airlines
Wed, Dec 18 - Thu, Dec 19
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$308 Roundtrip, found 22 hours ago
$308
Roundtrip
found 22 hours ago
Select Sun Country Airlines flight, departing Wed, Dec 18 from Sky Harbor Intl. to O'Hare Intl., returning Thu, Dec 19, priced at $308 found 22 hours ago

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 February, 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 $43, 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 $43 right now, why wait?

Winnetka Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$42

Last Minute Hotel Deals in Winnetka

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $143 per night from Dec 8 to Dec 9
$143
includes taxes & fees
Dec 8 - Dec 9
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,199 reviews)
"nice hotel, convenient location, very good restaurant, helpful staff. Unfortunately the Golden Room was closed and I couldn't see it. Of course the hotel is old, but my room was clean. so everything is fine"

Reviewed on Nov 30, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $120 per night from Jan 2 to Jan 3
$120
includes taxes & fees
Jan 2 - Jan 3, 2025
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (3,575 reviews)
"Always great stay"

Reviewed on Dec 1, 2024

River Hotel
Club Quarters Hotel, Central Loop, Chicago
Club Quarters Hotel, Central Loop, Chicago
4 out of 5
111 West Adams Street, Chicago, IL
The price is $119 per night from Jan 2 to Jan 3
$119
includes taxes & fees
Jan 2 - Jan 3, 2025
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
8.4/10 Very Good! (3,256 reviews)
Excelente
"Excelente relación calidad-precio. Muy centrico"

Reviewed on Nov 30, 2024

Club Quarters Hotel, Central Loop, Chicago
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
The price is $137 per night from Jan 2 to Jan 3
$137
includes taxes & fees
Jan 2 - Jan 3, 2025
Stay at this 4-star spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (2,766 reviews)
Interesting hotel. Great location.
"Arrived at hotel found a parking garage a few blocks away. Walked in there is a restaurant on ground floor and you take elevator or stairs up one level for lobby of hotel to check in. Instead of standing counter the staff sit at low desk. After checkin we went to room. It was nice with a nice view. ..."

Reviewed on Dec 1, 2024

Eurostars Magnificent Mile
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago
4.5 out of 5
909 North Michigan Ave, Chicago, IL
The price is $184 per night from Dec 15 to Dec 16
$184
includes taxes & fees
Dec 15 - Dec 16
Stay at this 4.5-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,006 reviews)
"Nice place, extremely overpriced. Great location!"

Reviewed on Nov 30, 2024

The Westin Michigan Avenue Chicago
Hotel Felix River North/Magnificent Mile
Hotel Felix River North/Magnificent Mile
4 out of 5
111 W Huron St, Chicago, IL
The price is $120 per night from Dec 23 to Dec 24
$120
includes taxes & fees
Dec 23 - Dec 24
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
7.8/10 Good! (1,298 reviews)
"It was clean. Great and friendly staff. Would stay again"

Reviewed on Dec 1, 2024

Hotel Felix River North/Magnificent Mile
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
The price is $125 per night from Dec 24 to Dec 25
$125
includes taxes & fees
Dec 24 - Dec 25
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very Good! (3,278 reviews)
"Best thing about the properly was that it had made to order breakfast and complimentary evening snacks along with daily two drinks per person on the house. This was unique I have found at this that I never experienced in any other Hilton properties. Not to mention the swimming pool was also open ..."

Reviewed on Dec 1, 2024

Embassy Suites by Hilton Chicago Downtown River North
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
The price is $108 per night from Dec 17 to Dec 18
$108
includes taxes & fees
Dec 17 - Dec 18
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
9.2/10 Wonderful! (2,318 reviews)
"It's an excellent hotel with fantastic amenities, a great location, and great value! The rooms are small, making them suitable for solo and intimate travel. This is not for a family. The shower door was not shutting fully, causing a bit of flooding. But other than that, it's a fantastic hotel. Breakfast ..."

Reviewed on Nov 30, 2024

citizenM Chicago Downtown
See all 4,110 properties in Winnetka
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.