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Winnetka

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Winnetka Flights as Low as $111

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

Frontier Airlines
Wed, May 28 - Mon, Jun 2
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$111 Roundtrip, found 5 days ago
$111
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, May 28 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Mon, Jun 2, priced at $111 found 5 days ago
Spirit Airlines
Sun, May 18 - Tue, May 20
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$132 Roundtrip, found 18 hours ago
$132
Roundtrip
found 18 hours ago
Select Spirit Airlines flight, departing Sun, May 18 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Tue, May 20, priced at $132 found 18 hours ago
Spirit Airlines
Sun, May 18 - Thu, May 22
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$142 Roundtrip, found 16 hours ago
$142
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Sun, May 18 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, May 22, priced at $142 found 16 hours ago
Frontier Airlines
Fri, May 30 - Mon, Jun 2
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$143 Roundtrip, found 2 days ago
$143
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, May 30 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Mon, Jun 2, priced at $143 found 2 days ago
Frontier Airlines
Wed, May 28 - Fri, May 30
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$145 Roundtrip, found 5 days ago
$145
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, May 28 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Fri, May 30, priced at $145 found 5 days ago
Spirit Airlines
Sun, Jun 1 - Thu, Jun 5
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$150 Roundtrip, found 9 hours ago
$150
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Sun, Jun 1 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, Jun 5, priced at $150 found 9 hours ago
Spirit Airlines
Thu, May 15 - Thu, May 22
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$150 Roundtrip, found 4 days ago
$150
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, May 15 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, May 22, priced at $150 found 4 days ago
Spirit Airlines
Thu, May 22 - Fri, May 30
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$167 Roundtrip, found 4 days ago
$167
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, May 22 from Southwest Florida Intl. to O'Hare Intl., returning Fri, May 30, priced at $167 found 4 days ago
Bargain Flight
Thu, May 22 - Sun, May 25
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$168 Roundtrip, found 13 hours ago
$168
Roundtrip
found 13 hours ago
Select Bargain Flight flight, departing Thu, May 22 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Sun, May 25, priced at $168 found 13 hours ago
Delta
Sat, Jun 7 - Sat, Jun 7
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$191 Roundtrip, found 18 hours ago
$191
Roundtrip
found 18 hours ago
Select Delta flight, departing Sat, Jun 7 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Sat, Jun 7, priced at $191 found 18 hours ago
American Airlines
Sat, Jun 14 - Wed, Jun 18
GSO
Piedmont Triad Intl.
ORD
O'Hare Intl.
$203 Roundtrip, found 1 day ago
$203
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jun 14 from Piedmont Triad Intl. to O'Hare Intl., returning Wed, Jun 18, priced at $203 found 1 day ago
JetBlue Airways
Wed, May 28 - Wed, Jun 4
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$214 Roundtrip, found 5 days ago
$214
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Wed, May 28 from Southwest Florida Intl. to O'Hare Intl., returning Wed, Jun 4, priced at $214 found 5 days ago
Delta
Sat, Jun 21 - Sat, Jun 21
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$215 Roundtrip, found 1 day ago
$215
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jun 21 from Southwest Florida Intl. to Midway Intl., returning Sat, Jun 21, priced at $215 found 1 day ago
Delta
Sun, May 25 - Tue, Jun 3
GSO
Piedmont Triad Intl.
MDW
Midway Intl.
$222 Roundtrip, found 23 hours ago
$222
Roundtrip
found 23 hours ago
Select Delta flight, departing Sun, May 25 from Piedmont Triad Intl. to Midway Intl., returning Tue, Jun 3, priced at $222 found 23 hours ago
Delta
Thu, May 1 - Tue, May 6
HSV
Huntsville Intl.
MDW
Midway Intl.
$311 Roundtrip, found 15 hours ago
$311
Roundtrip
found 15 hours ago
Select Delta flight, departing Thu, May 1 from Huntsville Intl. to Midway Intl., returning Tue, May 6, priced at $311 found 15 hours ago
Alaska Airlines
Mon, Jun 30 - Sun, Jul 6
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$11,654 Roundtrip, found 5 days ago
$11,654
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Mon, Jun 30 from Southwest Florida Intl. to O'Hare Intl., returning Sun, Jul 6, priced at $11,654 found 5 days 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 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 15 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 $111, 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 $111 right now, why wait?

Winnetka Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$111

Last Minute Hotel Deals in Winnetka

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 $189 per night from May 11 to May 12
$189
includes taxes & fees
May 11 - May 12
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! (3,954 reviews)
"Excellent location and very clean. Traveled solo with 2 kids and felt safe. Valet parking option needs better signage. Would absolutely stay here again."

Reviewed on Apr 27, 2025

Embassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $189 per night from May 27 to May 28
$189
includes taxes & fees
May 27 - May 28
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! (8,729 reviews)
"Amazing stay and people"

Reviewed on Apr 28, 2025

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is $181 per night from May 11 to May 12
$181
includes taxes & fees
May 11 - May 12
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,167 reviews)
"Everything excellent just in our room we struggled with hot water… but everything ok"

Reviewed on Apr 28, 2025

Hilton Chicago/Magnificent Mile Suites
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
The price is $235 per night from May 2 to May 3
$235
includes taxes & fees
May 2 - May 3
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and ...
"Great Customer Service! Great Stay! close to downtown Chicago !"

Reviewed on Apr 27, 2025

Swissotel - Chicago
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $164 per night from May 8 to May 9
$164
includes taxes & fees
May 8 - May 9
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! (4,101 reviews)
"Thus property was beautiful, very clean, friendly staff and there was free coffee. Amazing views made it even better. We walked across the street to the River Walk and down the block to a boat tour. We also walked to a bar and a restaurant downtown. If we go back to Chicago, we would definitely stay ..."

Reviewed on Apr 27, 2025

River Hotel
The Allegro Royal Sonesta Hotel Chicago Loop
The Allegro Royal Sonesta Hotel Chicago Loop
4 out of 5
171 W Randolph St, Chicago, IL
The price is $232 per night from May 11 to May 12
$232
includes taxes & fees
May 11 - May 12
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar ...
8.8/10 Excellent! (1,672 reviews)
"Lovely old hotel well maintained. Close to so many sights."

Reviewed on Apr 27, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
The price is $129 per night from May 26 to May 27
$129
includes taxes & fees
May 26 - May 27
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,021 reviews)
"Great stay."

Reviewed on Apr 28, 2025

Crowne Plaza Chicago West Loop by IHG
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
The price is $254 per night from May 11 to May 12
$254
includes taxes & fees
May 11 - May 12
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and ...
"The staff was friendly and helpful."

Reviewed on Apr 28, 2025

L7 Chicago by LOTTE
See all 4,134 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.