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Winnetka

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Winnetka Flights as Low as $88

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

Frontier Airlines
Sat, Oct 17 - Tue, Oct 20
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 21 hours ago
$88
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Sat, Oct 17 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Oct 20, priced at $88 found 21 hours ago
Frontier Airlines
Mon, Oct 5 - Thu, Oct 8
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$93 Roundtrip, found 13 hours ago
$93
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Mon, Oct 5 from Dallas-Fort Worth Intl. to Midway Intl., returning Thu, Oct 8, priced at $93 found 13 hours ago
Frontier Airlines
Wed, Oct 21 - Tue, Oct 27
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$100 Roundtrip, found 3 hours ago
$100
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Oct 21 from George Bush Intercontinental to O'Hare Intl., returning Tue, Oct 27, priced at $100 found 3 hours ago
Frontier Airlines
Fri, Oct 9 - Mon, Oct 26
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$126 Roundtrip, found 1 day ago
$126
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Oct 9 from Sky Harbor Intl. to O'Hare Intl., returning Mon, Oct 26, priced at $126 found 1 day ago
Bargain Flight
Tue, Sep 29 - Tue, Oct 6
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$199 Roundtrip, found 22 hours ago
$199
Roundtrip
found 22 hours ago
Select Bargain Flight flight, departing Tue, Sep 29 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Oct 6, priced at $199 found 22 hours ago
American Airlines
Wed, Oct 21 - Tue, Nov 3
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$209 Roundtrip, found 1 hour ago
$209
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Oct 21 from George Bush Intercontinental to O'Hare Intl., returning Tue, Nov 3, priced at $209 found 1 hour ago
Bargain Flight
Thu, Oct 8 - Sun, Oct 11
CHS
Charleston Intl.
ORD
O'Hare Intl.
$251 Roundtrip, found 13 hours ago
$251
Roundtrip
found 13 hours ago
Select Bargain Flight flight, departing Thu, Oct 8 from Charleston Intl. to O'Hare Intl., returning Sun, Oct 11, priced at $251 found 13 hours ago
Frontier Airlines
Sat, Dec 5 - Sat, Dec 12
IAH
George Bush Intercontinental
MDW
Midway Intl.
$258 Roundtrip, found 1 day ago
$258
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Dec 5 from George Bush Intercontinental to Midway Intl., returning Sat, Dec 12, priced at $258 found 1 day ago
Southwest Airlines
Tue, Oct 13 - Sat, Oct 17
DAL
Love Field
MDW
Midway Intl.
$261 Roundtrip, found 3 days ago
$261
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Oct 13 from Love Field to Midway Intl., returning Sat, Oct 17, priced at $261 found 3 days ago
Delta
Mon, Dec 21 - Thu, Dec 24
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$287 Roundtrip, found 3 days ago
$287
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Dec 21 from Sky Harbor Intl. to Midway Intl., returning Thu, Dec 24, priced at $287 found 3 days ago
Southwest Airlines
Thu, Oct 15 - Sun, Oct 18
CHS
Charleston Intl.
MDW
Midway Intl.
$383 Roundtrip, just found
$383
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Oct 15 from Charleston Intl. to Midway Intl., returning Sun, Oct 18, priced at $383 just found
Delta
Wed, Jun 23 - Sat, Jul 3
DAL
Love Field
ORD
O'Hare Intl.
$391 Roundtrip, found 2 days ago
$391
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jun 23 from Love Field to O'Hare Intl., returning Sat, Jul 3, priced at $391 found 2 days ago
American Airlines
Sat, Sep 26 - Sat, Oct 3
IAH
George Bush Intercontinental
RFD
Greater Rockford
$394 Roundtrip, found 3 days ago
$394
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Sep 26 from George Bush Intercontinental to Greater Rockford, returning Sat, Oct 3, priced at $394 found 3 days ago
American Airlines
Sat, Sep 26 - Tue, Sep 29
PHX
Sky Harbor Intl.
RFD
Greater Rockford
$486 Roundtrip, found 6 hours ago
$486
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Sat, Sep 26 from Sky Harbor Intl. to Greater Rockford, returning Tue, Sep 29, priced at $486 found 6 hours ago
American Airlines
Sat, Sep 26 - Mon, Sep 28
CHS
Charleston Intl.
RFD
Greater Rockford
$493 Roundtrip, found 13 hours ago
$493
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sat, Sep 26 from Charleston Intl. to Greater Rockford, returning Mon, Sep 28, priced at $493 found 13 hours ago
American Airlines
Fri, Sep 25 - Mon, Sep 28
DFW
Dallas-Fort Worth Intl.
RFD
Greater Rockford
$587 Roundtrip, found 3 hours ago
$587
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Fri, Sep 25 from Dallas-Fort Worth Intl. to Greater Rockford, returning Mon, Sep 28, priced at $587 found 3 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 October, 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 14 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 $88, 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 $88 right now, why wait?

Winnetka Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$82

Last Minute Hotel Deals in Winnetka

River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,446 reviews)
"It’s OK , well we did book on Expedia. It didn’t show us that we paid a club room which was like a very very very small room for about $600 which is crazy so then we had to go upgrade to a standard. I should think that they should definitely lower the pricing for two nights of that really really ..."

Reviewed on Sep 14, 2026

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River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (2,238 reviews)
"It’s definitely an older style hotel/room. Our first room was very small. Our second room was much nicer and bigger. We also had Chicago police knock on a neighbors door, which of course would make you not at ease. I loved the location. Just probably wouldn’t stay again."

Reviewed on Sep 14, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,246 reviews)
"Wasn’t bad thank you"

Reviewed on Sep 14, 2026

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Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (3,211 reviews)
"They cancelled my booking and no one told me. I was stuck in Chicago without a hotel. Neither Expedia nor the hotel emailed or called me about this cancelled booking"

Reviewed on Sep 14, 2026

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Hilton Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (2,168 reviews)
"This is my favorite hotel in Chicago! We always choose it when we come for fun or for hospital stays! I have always found the staff to be so friendly and helpful. I love the vibe of the hotel and the location is perfect with coffee shops and restaurants. The roof top bar is one of my favorite perks. ..."

Reviewed on Sep 14, 2026

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The Chicago Hotel Collection - Magnificent Mile
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 out of 5
160 E Huron Street Chicago IL
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the ...
8/10 Very Good! (1,613 reviews)
"Terrible experience. They double charged me for the “deposit” but it was two different amounts. Went to the front desk to ask and they said they don’t have a record of it but it clearly shows on my bank statement. When I checked out, a few hours later they charged me again, twice!! With 2 other completely ..."

Reviewed on Sep 14, 2026

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Hampton Inn Chicago Downtown/Magnificent Mile
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
225 N Wabash Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...
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L7 Chicago by LOTTE
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
201 East Walton Place Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
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Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
See all 4,413 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.