Cheap flights To Winnetka (CHI) from $29

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Cheap Flights to Winnetka from $29 One Way, $56 Round Trip

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

Thu, Apr 23 - Wed, Apr 29
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$56 Roundtrip, found 19 hours ago
$56
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Thu, Apr 23 from Newark Liberty Intl. Airport to Midway Intl., returning Wed, Apr 29, priced at $56 found 19 hours ago
Tue, May 5 - Thu, May 7
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$58 Roundtrip, found 5 days ago
$58
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, May 5 from Dallas-Fort Worth Intl. to Midway Intl., returning Thu, May 7, priced at $58 found 5 days ago
Wed, Apr 15 - Thu, Apr 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$59 Roundtrip, found 11 hours ago
$59
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Wed, Apr 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Apr 16, priced at $59 found 11 hours ago
Wed, Apr 15 - Wed, Apr 22
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$60 Roundtrip, found 5 days ago
$60
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Apr 15 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Apr 22, priced at $60 found 5 days ago
Tue, Apr 21 - Tue, Apr 21
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Apr 21 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Apr 21, priced at $68 found 1 day ago
Sat, Apr 25 - Wed, Apr 29
LGA
LaGuardia
ORD
O'Hare Intl.
$87 Roundtrip, found 15 hours ago
$87
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Sat, Apr 25 from LaGuardia to O'Hare Intl., returning Wed, Apr 29, priced at $87 found 15 hours ago
Thu, Apr 16 - Mon, Apr 20
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$97 Roundtrip, found 2 hours ago
$97
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Thu, Apr 16 from Newark Liberty Intl. Airport to O'Hare Intl., returning Mon, Apr 20, priced at $97 found 2 hours ago
Sat, May 2 - Tue, May 5
LGA
LaGuardia
MDW
Midway Intl.
$144 Roundtrip, found 1 day ago
$144
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 2 from LaGuardia to Midway Intl., returning Tue, May 5, priced at $144 found 1 day ago
Sat, Apr 25 - Sat, May 2
LGA
LaGuardia
RFD
Greater Rockford
$167 Roundtrip, found 5 days ago
$167
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Apr 25 from LaGuardia to Greater Rockford, returning Sat, May 2, priced at $167 found 5 days ago
Wed, May 27 - Fri, May 29
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$170 Roundtrip, found 5 days ago
$170
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, May 27 from Newark Liberty Intl. Airport to Greater Rockford, returning Fri, May 29, priced at $170 found 5 days ago

Winnetka Flight Information

Traveling To
Winnetka
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, American Airlines
Flight Price
$56
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Winnetka economy flight packages

Price found within the past 48 hours. Click for updated prices.
Eurostars Magnificent Mile
4.0-star property

Eurostars Magnificent Mile

May 22 - May 24

2 night stay

Atlanta (ATL) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Atlanta (ATL)

Frontier Airlines • Coach
Price was $710, price is now $504 per person
$504
per person
found 1 day ago
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

May 1 - May 4

3 night stay

Atlanta (ATL) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $817, price is now $586 per person
$586
per person
found 18 hours ago
Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

May 22 - May 24

2 night stay

Atlanta (ATL) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Atlanta (ATL)

Frontier Airlines • Coach
Price was $741, price is now $552 per person
$552
per person
found 1 day ago
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Winnetka first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (3,495 reviews)

May 13 - May 15

2 night stay

Atlanta (ATL) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Atlanta (ATL)

United • FirstClass
Price was $865, price is now $693 per person
$693
per person
found 8 hours ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.

Reviewed on Jan 14, 2026

Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

8.6/10 Excellent! (2,076 reviews)

May 13 - May 15

2 night stay

Atlanta (ATL) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Atlanta (ATL)

United • FirstClass
Price was $958, price is now $786 per person
$786
per person
found 8 hours ago
The room was great the service was good

Reviewed on Feb 16, 2026

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,852 reviews)

May 13 - May 15

2 night stay

Atlanta (ATL) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Atlanta (ATL)

United • FirstClass
Price was $1,288, price is now $1,086 per person
$1,086
per person
found 8 hours ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!

Reviewed on Oct 13, 2025

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Winnetka

Orbitz makes it easy for you to find cheap prices for flights to Winnetka. When you search for your tickets on Orbitz, you don’t have to look any further for the best Winnetka flights available ever again.

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Orbitz understands that your travel plans may change. That’s why we make it simple to cancel your ticket for Winnetka flights if necessary. All you have to do is contact the Orbitz Customer Service department to adjust your travel plans after booking. When you’re ready book your trip, just do a fresh search for the perfect flights to Winnetka again.

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Low Prices for Winnetka Flights

Orbitz has the scoop on cheap tickets and bargain airfare for flights to Winnetka. You can research the best flights for your trip and make your reservations all on our website with the confidence that you’re getting a great price.

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Frequently asked questions

Which airlines fly to Winnetka?
You can choose from 20 airlines with flights to O'Hare Intl. Airport (ORD), the most popular airport in the city. With all that choice, you're certain to unearth an amazing deal. Here are some of the international carriers that'll get you to Winnetka — and then exploring every part of this city:

  • United Airlines - 612 flights to Winnetka per month
  • American Airlines - 339 flights to Winnetka per month
  • Air Canada - 190 flights to Winnetka per month

What is the best airport to fly to in Winnetka?
Lock in a flight to O'Hare Intl. Airport (ORD) and you'll be enjoying this popular city in next to no time. This airport is approximately 12 miles southwest of the center of town. But ORD isn't your only option. Midway Intl. Airport (MDW) also services Winnetka, so compare flight prices to snap up the best deal.
How much is a flight to Winnetka?
Loads of fabulous deals were on offer this week, with return flights to Winnetka ranging from $56 to $170. But it was jet-setters flying in from New York (EWR) who landed the really big bargains. One-way flights to Winnetka started at just $29.
How to book the cheapest flight to Winnetka?
Using Orbitz, you'll find some of the most affordable flight deals around from a wide selection of airlines. But if you'd like to increase your chances of snapping up cheap flights to Winnetka, here are a few tips to consider:

  • Depending on your departure city, click on the 'Nearby airports' function (located under the departure and arrival form fields). In some instances, alternative departure points offer better value for money.
  • If you're flexible with when you take off, click on the 'Show flexible dates' link. It'll display the flight deals for the days before and after your chosen departure. Airfares often vary depending on what day it is.
  • You can also hit the 'Show options' function to filter results for your preferred airline, seating class, and nonstop and refundable flights. Under 'Sort & Filter' to the left, you can even pick the time of day you'd prefer to fly.
  • Once you've sorted out your travel dates, don't wait to book. Fares generally get more expensive as the departure date nears.
  • Make greater savings on your adventure by bundling your hotel, flights and car rentals into a package. Your credit card will thank you for it.
  • Don't fly during the busy season if you can. By avoiding school vacations and summer, you can save a significant amount on your airfare.

How long is a flight to Winnetka?
The U.S. Is big, so that depends on which airport you're departing from. To make vacation planning a bit easier, we've selected three of the most well-known routes to Winnetka and calculated their average flight times:

  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 2 hours and 40 minutes
  • Boston, MA (BOS-Logan Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 51 minutes
  • Washington, DC (DCA-Ronald Reagan Washington National) to O'Hare Intl. Airport (ORD) - 2 hours and 13 minutes

What is the best time to book a flight to Winnetka?
Purchase your tickets to Winnetka in January. This is the best time of the year for bargain prices, followed by February and August. Snap up cheap flights and let your dream vacation come true with Orbitz.
What day of the week is the cheapest to book a flight to Winnetka?
When it comes to cheap fares to Winnetka, the best days to make a booking are generally Tuesdays, Wednesdays and Saturdays. An unbeatable flight deal is just clicks away with Orbitz.
What is the cheapest day of the week to fly to Winnetka?
Think about flying early in the week to get cheap flights to Winnetka. Orbitz data from 2020 shows Monday is normally the most inexpensive day to fly out, followed by Tuesday. Saturdays were shown to have the highest airfares. This is probably because many travelers prefer to begin their vacation after a long working week.
What is the cheapest month to fly to Winnetka?
To book cheap flights to Winnetka, you should take off in August. If saving money on your ticket is your main priority, Orbitz data has found that this is generally the best month to take a trip. June is when fares are the most expensive.
Which airlines allow free cancellation?
We know that plans can change and flexibility matters. That's why you can easily search for flights that have free cancellation and no change fees on Orbitz. Just click on "Filter by flexible change policies" and we'll find you fares with more flexibility than a crayon left in the sun!
What do I need for the flight to Winnetka?
Flying can be fun with a little pre-planning! Make your journey a total breeze with the following useful hints:

  • Before you step foot on the plane, you'll need to present proof of identification, such as your passport. You'll also need your ticket. If you're traveling with the kids, check with your airline about which documents they may need.
  • Make time fly by even faster on your short hop by packing the right stuff. Think snacks, a water bottle and entertainment. If you'd like your trip to Winnetka to go quietly, squeeze some noise-canceling headphones or earplugs into your carry-on bag too.
  • It can get chilly on the plane. If you'd prefer not to shiver your way through the flight, wear an extra layer.

How many direct flights are there to Winnetka?
Your next amazing adventure is one easy plane trip away, with 2,332 direct flights to Winnetka every month. Search for a suitable flight with Orbitz and lock in a rewarding deal with United Airlines, American Airlines or Delta Air Lines. Other popular airlines that provide nonstop services include Southwest Airlines, Spirit Airlines and Air Canada.
How do I get cheap first-class/business deals to Winnetka?
If you think a business or first-class airfare is out of your reach, think again. Here are some terrific tips to help you score a premium flight to Winnetka for less:

  • Flexibility is important. By being open to different travel dates, you'll have better odds of spotting a sale on business or first-class airfares.
  • Budget airlines offer first or business-class seats at more affordable prices. Give the full-service carriers a miss and check out these cheaper options.
  • Bid for an upgrade in online auctions (if available) or upgrade your fare through your frequent flyer program.

How to get into Winnetka from the airport?
If you enjoy the flexibility that comes with having your own wheels, reserve an O'Hare Intl. Airport (ORD) car rental with one of the reputable providers at O'Hare Intl. Airport (ORD). Thrifty Car Rental and Dollar have some fantastic rides to choose from. Once you've grabbed the keys, the heart of Winnetka is around 12 miles to the northeast. Or, maybe you'd rather take a taxi into town and rent a vehicle from the downtown area after you've mastered the lay of the land? Winnetka car rentals always has loads of bargains available.
Travel tips for Winnetka

  • Downtown Winnetka is packed with excellent attractions. Spots like Wagner Farm and Mitchell Museum of the American Indian will keep your feet moving and the sightseer in you happy.
  • If you're in the mood for a fun day trip, there are more sights waiting to impress you a quick commute from the center. Find out why Wrigley Field and McCormick Place are on the to-do lists of many Winnetka visitors.
  • Eager to find out what else Winnetka has to offer? Pick up a car rental and hotfoot it to Calumet City or Naperville — or both! With your own ride, discovering those off-radar destinations will also be a cinch.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.