Cheap flights To Winnetka (CHI) from $29

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights to Winnetka from $29 One Way, $58 Round Trip

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

Sun, Jan 25 - Mon, Feb 2
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$58 Roundtrip, found 2 hours ago
$58
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sun, Jan 25 from John F. Kennedy Intl. to O'Hare Intl., returning Mon, Feb 2, priced at $58 found 2 hours ago
Tue, Jan 13 - Sun, Jan 18
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$59 Roundtrip, found 2 days ago
$59
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Jan 13 from Newark Liberty Intl. Airport to Midway Intl., returning Sun, Jan 18, priced at $59 found 2 days ago
Sat, Feb 21 - Sat, Feb 28
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$59 Roundtrip, found 6 hours ago
$59
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sat, Feb 21 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Feb 28, priced at $59 found 6 hours ago
Sat, Feb 21 - Sat, Feb 28
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$59 Roundtrip, found 6 hours ago
$59
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Sat, Feb 21 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Feb 28, priced at $59 found 6 hours ago
Tue, Jan 20 - Tue, Jan 20
LGA
LaGuardia
ORD
O'Hare Intl.
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jan 20 from LaGuardia to O'Hare Intl., returning Tue, Jan 20, priced at $63 found 1 day ago
Fri, Jan 30 - Fri, Feb 6
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$72 Roundtrip, found 1 hour ago
$72
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Fri, Jan 30 from Newark Liberty Intl. Airport to O'Hare Intl., returning Fri, Feb 6, priced at $72 found 1 hour ago
Fri, Feb 20 - Mon, Feb 23
LGA
LaGuardia
ORD
O'Hare Intl.
$97 Roundtrip, found 9 hours ago
$97
Roundtrip
found 9 hours ago
Select United flight, departing Fri, Feb 20 from LaGuardia to O'Hare Intl., returning Mon, Feb 23, priced at $97 found 9 hours ago
Sat, Jan 31 - Mon, Feb 2
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 13 hours ago
$97
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Sat, Jan 31 from John F. Kennedy Intl. to O'Hare Intl., returning Mon, Feb 2, priced at $97 found 13 hours ago
Wed, Feb 11 - Mon, Feb 16
LGA
LaGuardia
MDW
Midway Intl.
$97 Roundtrip, found 8 hours ago
$97
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Wed, Feb 11 from LaGuardia to Midway Intl., returning Mon, Feb 16, priced at $97 found 8 hours ago
Fri, Jan 16 - Fri, Jan 23
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$98 Roundtrip, found 1 hour ago
$98
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Fri, Jan 16 from John F. Kennedy Intl. to O'Hare Intl., returning Fri, Jan 23, priced at $98 found 1 hour ago

Winnetka Flight Information

Traveling To
Winnetka
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, United, Southwest Airlines, JetBlue Airways, American Airlines
Flight Price
$58
Earliest Departing Flight
Latest Departing Flight

Flights Review

Mar 10, 2018

Great overall service. Smooth landing. Plane was even early.

A verified traveler
Denver to Chicago · United

Book Your Flight & Hotel Together & Save

Winnetka economy flight packages

Price found within the past 48 hours. Click for updated prices.
Destination Geneva National
4.0-star property

Destination Geneva National

Jan 30 - Feb 2

3 night stay

Houston (IAH) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $402, price is now $258 per person
$258
per person
found 1 day ago
La Banque Hotel
4.0-star property

La Banque Hotel

Jan 30 - Feb 2

3 night stay

Houston (IAH) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $617, price is now $368 per person
$368
per person
found 1 day ago
Hilton Grand Vacations Club Chicago Magnificent Mile
3.5-star property

Hilton Grand Vacations Club Chicago Magnificent Mile

Feb 18 - Feb 24

6 night stay

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

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $790, price is now $510 per person
$510
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Houston to Winnetka
View all trips

Winnetka

Traveling to Winnetka and need a cheap flight? Orbitz has great deals on flights to Winnetka right now. Plus, we offer big discounts on hotel rooms and car rentals for a great money-saving trip.

Find Low Cost Flights to Winnetka Quickly and Hassle-Free

There are many Internet sites that promise cheap Winnetka flights, but a busy, bargain-minded trip planner needs more than just budget air tickets. Not only does Orbitz offer the best deals for domestic and international air fare, but we also provide the resources and tools to help you plan your flights to Winnetka, book your lodging, and look up key attractions in Winnetka. Our easy search tools and guaranteed low prices let you budget your time and your money so you have more of both to spend on your vacation.

New Apps Make Booking Winnetka Flights Easier Than Ever

You no longer need to be sitting at your computer to find amazing Orbitz sales for flights to Winnetka now we offer cutting-edge mobile tools for many Android and iOS gadgets. These free apps allow you to run a search for discount air fare, look for special vacation packages, or check on your booked Winnetka flights from any location. Some special deals are only available for mobile customers, so be sure to take advantage of these free downloads today.

Orbitz Customers Are Truly #1

Orbitz takes pride in providing the best customer experience possible, and that effort doesn't end with discount flights to Winnetka or user-friendly mobile apps and web tools. Orbitz Customer Service is always ready to answer questions and help you with booking, planning, or canceling your Winnetka flights. When you need us, we’re here for you!

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 $58 to $98. But it was jet-setters flying in from New York (JFK) 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.