Cheap flights To Winnetka (CHI) from $39

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Cheap Flights to Winnetka from $39 One Way, $69 Round Trip

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

Sat, May 31 - Wed, Jun 4
LGA
LaGuardia
ORD
O'Hare Intl.
$69 Roundtrip, found 9 hours ago
$69
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Sat, May 31 from LaGuardia to O'Hare Intl., returning Wed, Jun 4, priced at $69 found 9 hours ago
Wed, May 28 - Thu, May 29
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$77 Roundtrip, just found
$77
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, May 28 from Newark Liberty Intl. Airport to O'Hare Intl., returning Thu, May 29, priced at $77 just found
Fri, May 30 - Tue, Jun 3
LGA
LaGuardia
ORD
O'Hare Intl.
$79 Roundtrip, just found
$79
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, May 30 from LaGuardia to O'Hare Intl., returning Tue, Jun 3, priced at $79 just found
Wed, May 28 - Wed, May 28
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$80 Roundtrip, just found
$80
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, May 28 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, May 28, priced at $80 just found
Tue, May 27 - Sat, May 31
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$81 Roundtrip, found 1 hour ago
$81
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Tue, May 27 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sat, May 31, priced at $81 found 1 hour ago
Sat, May 24 - Tue, May 27
LGA
LaGuardia
ORD
O'Hare Intl.
$81 Roundtrip, just found
$81
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, May 24 from LaGuardia to O'Hare Intl., returning Tue, May 27, priced at $81 just found
Tue, May 27 - Wed, May 28
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$83 Roundtrip, just found
$83
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, May 27 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, May 28, priced at $83 just found
Wed, May 7 - Wed, May 28
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$88 Roundtrip, found 3 days ago
$88
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Wed, May 7 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, May 28, priced at $88 found 3 days ago
Wed, May 14 - Wed, May 28
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 17 hours ago
$100
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Wed, May 14 from Los Angeles Intl. to O'Hare Intl., returning Wed, May 28, priced at $100 found 17 hours ago
Wed, May 14 - Tue, May 27
LGA
LaGuardia
ORD
O'Hare Intl.
$139 Roundtrip, found 1 day ago
$139
Roundtrip
found 1 day ago
Select United flight, departing Wed, May 14 from LaGuardia to O'Hare Intl., returning Tue, May 27, priced at $139 found 1 day ago

Winnetka ORD Flight Information

Traveling To
Winnetka
Destination Airport IATA Code
CHI
Number of Airlines Serving
16
Airlines
Spirit Airlines, United
Flight Price
$69
Earliest Departing Flight
AA 3446 5:56AM EDT
Latest Departing Flight
IB 4838 May 8 6:46PM EDT

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.
Motel 6 Joliet, IL - I-80
2.0-star property

Motel 6 Joliet, IL - I-80

Jun 6 - Jun 8

2 night stay

Dallas (DFW) to Chicago (CHI)

Frontier Airlines • Coach

Chicago (CHI) to Dallas (DFW)

Spirit Airlines • Coach
per person
found 5 hours ago
Hyatt Regency O'Hare Chicago
4.0-star property

Hyatt Regency O'Hare Chicago

Jun 12 - Jun 15

3 night stay

Baltimore (BWI) to Chicago (ORD)

Spirit Airlines • Coach

Chicago (ORD) to Baltimore (BWI)

Delta • Coach
per person
found 1 day ago
Sonesta Simply Suites Lansing
2.5-star property

Sonesta Simply Suites Lansing

Jun 6 - Jun 8

2 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Coach

Chicago (ORD) to Dallas (DFW)

Spirit Airlines • Coach
per person
found 5 hours ago
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Winnetka premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago/Magnificent Mile Suites
3.5-star property

Hilton Chicago/Magnificent Mile Suites

8.8/10 Excellent! (2,064 reviews)

Jun 27 - Jun 30

3 night stay

Washington (DCA) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 19 hours ago
We had a great stay and would definitely return! We liked the location—everything we needed was close by, and we felt completely safe traveling as a group of women with a child. The hotel was within walking distance to fabulous shopping and dining, which made our trip extra enjoyable. For anyone planning to explore beyond the immediate area, we highly recommend getting a bus or “L” pass. Public transportation was easy to navigate and made getting around the city a breeze. One of the highlights of our stay was the incredibly kind and welcoming bellman (we regret not getting his name!). He went out of his way to make us feel at home, and that warm hospitality really stood out. The only downside was the sleeper sofa—the mattress could definitely use an upgrade for better comfort. Overall, we had a great experience and would recommend this hotel to others.

Reviewed on Apr 24, 2025

Omni Chicago Hotel
4.5-star property

Omni Chicago Hotel

9/10 Wonderful! (1,444 reviews)

Jun 27 - Jun 30

3 night stay

Washington (DCA) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 19 hours ago
Favorite place to stay whenever I’m in Chicago!

Reviewed on Dec 28, 2024

Arlo Chicago
4.0-star property

Arlo Chicago

9.2/10 Wonderful! (1,665 reviews)

Jun 27 - Jun 30

3 night stay

Washington (DCA) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 19 hours ago
Nice hotel. Great location. Nice room. Pictures made hotel seem like it was so much more. It was just one small hallway. Nothing more. Very disappointed with the lobby. I thought by the pictures I was getting so much more! Payed a $150 resort fee for two night. There was absolutely no resort and no resort benefits. That was purely a money grab. Didn’t even get my room cleaned each day. Nice room. Nice hotel. Just less that I thought!

Reviewed on Oct 13, 2024

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Winnetka first class flight packages

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

Arlo Chicago

9.2/10 Wonderful! (1,665 reviews)

Jun 13 - Jun 16

3 night stay

Washington (DCA) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Washington (DCA)

Delta • FirstClass
per person
found 5 hours ago
Nice hotel. Great location. Nice room. Pictures made hotel seem like it was so much more. It was just one small hallway. Nothing more. Very disappointed with the lobby. I thought by the pictures I was getting so much more! Payed a $150 resort fee for two night. There was absolutely no resort and no resort benefits. That was purely a money grab. Didn’t even get my room cleaned each day. Nice room. Nice hotel. Just less that I thought!

Reviewed on Oct 13, 2024

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (1,605 reviews)

Jun 13 - Jun 16

3 night stay

Washington (DCA) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Washington (DCA)

Delta • FirstClass
per person
found 5 hours ago
Our second time. Here, highly recommended

Reviewed on Mar 3, 2025

Omni Chicago Hotel
4.5-star property

Omni Chicago Hotel

9/10 Wonderful! (1,444 reviews)

Jun 13 - Jun 16

3 night stay

Washington (DCA) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Washington (DCA)

Delta • FirstClass
per person
found 5 hours ago
Favorite place to stay whenever I’m in Chicago!

Reviewed on Dec 28, 2024

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Winnetka

Get the absolute lowest prices on flights to Winnetka by shopping with Orbitz. Orbitz is the most efficient travel planner around, allowing you to search, compare and book discount domestic and international flights fast. With cutting-edge mobile tools and access to frequent flier rewards programs, we have everything you need for both your routine and holiday excursions.

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Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Winnetka flights. Mobile apps can also be used to share travel itineraries with family members or business associates.

Keeping Everyone Up To Date

When you download the free Orbitz mobile phone app, you can get regular and free flight updates. These will keep you informed of important scheduling changes. Updates can even be sent to several contacts, helping to keep everyone current on anticipated arrival times and all other relevant flight details.

Orbitz makes traveling on a budget very easy to do. We provide everything you need to plan your ideal trip from start to finish. Getting there and back again is a snap when you book your Winnetka flight using Orbitz.

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 $69 to $139. 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 $39.
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.