Cheap flights To Winnetka (CHI) from $29

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Cheap Flights to Winnetka from $29 One Way, $60 Round Trip

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

Wed, Aug 20 - Tue, Aug 26
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, Aug 20 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Aug 26, priced at $60 found 5 days ago
Wed, Oct 8 - Tue, Oct 14
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$70 Roundtrip, found 6 days ago
$70
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Oct 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Oct 14, priced at $70 found 6 days ago
Wed, Aug 27 - Wed, Sep 10
LGA
LaGuardia
ORD
O'Hare Intl.
$71 Roundtrip, found 16 hours ago
$71
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Wed, Aug 27 from LaGuardia to O'Hare Intl., returning Wed, Sep 10, priced at $71 found 16 hours ago
Thu, Oct 16 - Thu, Oct 23
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$88 Roundtrip, found 4 days ago
$88
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Oct 16 from Newark Liberty Intl. Airport to Midway Intl., returning Thu, Oct 23, priced at $88 found 4 days ago
Wed, Sep 3 - Wed, Sep 10
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$97 Roundtrip, just found
$97
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Sep 3 from Los Angeles Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $97 just found
Thu, Jan 8 - Mon, Jan 12
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$100 Roundtrip, found 11 hours ago
$100
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Thu, Jan 8 from Newark Liberty Intl. Airport to O'Hare Intl., returning Mon, Jan 12, priced at $100 found 11 hours ago
Tue, Nov 11 - Tue, Nov 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Nov 11 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Nov 11, priced at $132 found 1 day ago
Sat, Sep 20 - Wed, Sep 24
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$137 Roundtrip, found 3 days ago
$137
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Sep 20 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 24, priced at $137 found 3 days ago
Wed, Oct 22 - Sat, Oct 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 11 hours ago
$137
Roundtrip
found 11 hours ago
Select United flight, departing Wed, Oct 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Oct 25, priced at $137 found 11 hours ago
Wed, Oct 22 - Sat, Oct 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 11 hours ago
$137
Roundtrip
found 11 hours ago
Select Delta flight, departing Wed, Oct 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Oct 25, priced at $137 found 11 hours ago

Winnetka Flight Information

Traveling To
Winnetka
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Spirit Airlines, Frontier Airlines, Delta, Southwest Airlines, United, American Airlines
Flight Price
$60
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.
AmericInn by Wyndham Princeton IL
2.5-star property

AmericInn by Wyndham Princeton IL

Sep 24 - Sep 30

6 night stay

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

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 hour ago
Harrah's Joliet Casino & Hotel
3.5-star property

Harrah's Joliet Casino & Hotel

Sep 4 - Sep 7

3 night stay

Los Angeles (LAX) to Chicago (CHI)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 19 hours ago
The Allegro Royal Sonesta Hotel Chicago Loop
4.0-star property

The Allegro Royal Sonesta Hotel Chicago Loop

Sep 11 - Sep 15

4 night stay

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

United • Coach

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

Spirit Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
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Winnetka

Reach your destination without breaking your budget by booking your flights to Winnetka using Orbitz. We offer access to all of the best discounts on airfare, travel accommodations and even car rentals. Planning your trip and saving money are easier with Orbitz.

Get Discount Rates On Your Winnetka Flight

Whether planning ahead or deciding to book your trip at the last minute, Orbitz will provide the lowest rates on Winnetka flights. Using our free mobile phone apps will make you privy to a number of discounts that are unique to mobile phone users. These are perfect for harried travelers who want to find deals that they can qualify for on the same day.

Make Orbitz Your Official Travel Planner

Orbitz can be used for much more than comparing and booking a discount flight to Winnetka. We also offer a variety of resources for securing the ideal travel accommodations while staying on budget. Travel tips, hotel reviews, customized suggestions and even detailed images can all be accessed through your mobile phone.

Build A Comprehensive Travel Itinerary

In addition to booking a low cost flight to Winnetka, you can learn about the best places to visit, the best hotels to stay in and the preferred times for traveling. When you use Orbitz mobile phone apps you can also share your travel itineraries with friends and family members, all with just a few quick taps.

Using Orbitz to secure your Winnetka flights can save you money and time. Perfect for both the early travel planner and the last minute journey: Orbitz offers phenomenal customer service and unbeatable convenience.

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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 $60 to $137. But it was jet-setters flying in from New York (LGA) 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.

Nearby

Flights To

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.