Cheap flights To Winnetka (CHI) from $57

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Cheap Flights to Winnetka from $57 One Way, $128 Round Trip

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

Wed, Jul 8 - Sat, Jul 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$128 Roundtrip, found 5 hours ago
$128
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Wed, Jul 8 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Jul 11, priced at $128 found 5 hours ago
Sat, Jul 11 - Sat, Jul 25
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$148 Roundtrip, found 1 day ago
$148
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jul 11 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Jul 25, priced at $148 found 1 day ago
Wed, Jul 8 - Sat, Jul 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$149 Roundtrip, found 5 hours ago
$149
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Wed, Jul 8 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Jul 11, priced at $149 found 5 hours ago
Tue, Jul 14 - Wed, Jul 15
LGA
LaGuardia
RFD
Greater Rockford
$176 Roundtrip, found 4 days ago
$176
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Jul 14 from LaGuardia to Greater Rockford, returning Wed, Jul 15, priced at $176 found 4 days ago
Wed, Aug 19 - Wed, Aug 26
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$176 Roundtrip, found 20 hours ago
$176
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Wed, Aug 19 from Newark Liberty Intl. Airport to Greater Rockford, returning Wed, Aug 26, priced at $176 found 20 hours ago
Thu, Aug 20 - Mon, Aug 24
LGA
LaGuardia
ORD
O'Hare Intl.
$177 Roundtrip, found 9 hours ago
$177
Roundtrip
found 9 hours ago
Select Delta flight, departing Thu, Aug 20 from LaGuardia to O'Hare Intl., returning Mon, Aug 24, priced at $177 found 9 hours ago
Thu, Jul 23 - Mon, Jul 27
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$177 Roundtrip, found 2 hours ago
$177
Roundtrip
found 2 hours ago
Select United flight, departing Thu, Jul 23 from Newark Liberty Intl. Airport to O'Hare Intl., returning Mon, Jul 27, priced at $177 found 2 hours ago
Sat, Jul 11 - Tue, Jul 14
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$177 Roundtrip, found 19 hours ago
$177
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Sat, Jul 11 from John F. Kennedy Intl. to O'Hare Intl., returning Tue, Jul 14, priced at $177 found 19 hours ago
Wed, Jul 22 - Wed, Jul 29
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jul 22 from John F. Kennedy Intl. to O'Hare Intl., returning Wed, Jul 29, priced at $177 found 2 days ago
Wed, Aug 12 - Wed, Aug 12
LGA
LaGuardia
MDW
Midway Intl.
$177 Roundtrip, just found
$177
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Aug 12 from LaGuardia to Midway Intl., returning Wed, Aug 12, priced at $177 just found

Winnetka Flight Information

Traveling To
Winnetka
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Southwest Airlines, United, American Airlines, Delta
Flight Price
$128
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.
The Talbott, Autograph Collection
4.5-star property

The Talbott, Autograph Collection

Jun 28 - Jul 2

4 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $786, price is now $505 per person
$505
per person
found 1 day ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Jun 28 - Jul 2

4 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $953, price is now $572 per person
$572
per person
found 1 day ago
Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

Jun 28 - Jul 2

4 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $910, price is now $599 per person
$599
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Winnetka
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Winnetka premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sonesta Chicago O'Hare Airport Rosemont
3.0-star property

Sonesta Chicago O'Hare Airport Rosemont

8.6/10 Excellent! (1,746 reviews)

Jul 10 - Jul 13

3 night stay

New York (JFK) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $654, price is now $523 per person
$523
per person
found 16 hours ago
Room was excellent, clean and comfortable. Staff was freindly and helpful.

Reviewed on Jan 16, 2026

Staybridge Suites Chicago O'Hare - Rosemont by IHG
3.0-star property

Staybridge Suites Chicago O'Hare - Rosemont by IHG

9.2/10 Wonderful! (1,190 reviews)

Jul 10 - Jul 13

3 night stay

New York (JFK) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $741, price is now $607 per person
$607
per person
found 16 hours ago
Friendly staff, clean property

Reviewed on Apr 12, 2026

Holiday Inn Chicago O'Hare – Rosemont by IHG
3.0-star property

Holiday Inn Chicago O'Hare – Rosemont by IHG

9/10 Wonderful! (2,964 reviews)

Jul 10 - Jul 13

3 night stay

New York (JFK) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $674, price is now $558 per person
$558
per person
found 16 hours ago
Staff was so kind, shuttle drivers were amazing both in the middle of the night and the morning.

Reviewed on Feb 20, 2026

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Winnetka

Save more on flights to Winnetka while making top-quality travel arrangements. At Orbitz we provide access to low cost flights, hotel lodgings and other discounts, along with superior customer service and an unbeatable satisfaction guarantee.

Compare And Book Discount Flights to Winnetka

Now it is easier than ever to find a discount Winnetka flight. Orbitz users can compare airfares for both international and domestic flights and can quickly determine the best hotels and car rental companies to use. You may also check out hotel and other reviews along with a number of travel tips, making your visit to an unfamiliar destination enjoyable and hassle-free.

Use Your Mobile Phone To Secure A Low Cost Flight To Winnetka

We now offer free apps for the most commonly used mobile devices. You can use your mobile phone to share relevant information pertaining to your trips, view images of local lodgings and take advantage of hotel and car rental discounts that may be available only to mobile device users.

Boost Your Frequent Flyer Rewards

You even retain your ability to earn frequent flier points and rewards when purchasing your tickets with Orbitz for Winnetka flights. Enter your frequent flyer information into your Orbitz profile to start earning rewards.

You will find that Orbitz is a very low cost, yet very effective travel planner. Free updates via your mobile phone device will help to keep you and all relevant parties informed of important flight updates. With access to unbeatable sales on all travel essentials, Orbitz makes booking an affordable flight to Winnetka a breeze.

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 $128 to $177. But it was jet-setters flying in from Dallas (DFW) who landed the really big bargains. One-way flights to Winnetka started at just $57.
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.