Cheap flights To Winnetka (CHI) from $39

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Cheap Flights to Winnetka from $39 One Way, $77 Round Trip

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

Thu, Nov 13 - Mon, Nov 17
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$77 Roundtrip, found 2 hours ago
$77
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Thu, Nov 13 from Minneapolis - St. Paul Intl. to Midway Intl., returning Mon, Nov 17, priced at $77 found 2 hours ago
Wed, Nov 5 - Wed, Nov 12
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$77 Roundtrip, found 17 hours ago
$77
Roundtrip
found 17 hours ago
Select United flight, departing Wed, Nov 5 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Wed, Nov 12, priced at $77 found 17 hours ago
Thu, Nov 13 - Mon, Nov 17
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$82 Roundtrip, found 2 hours ago
$82
Roundtrip
found 2 hours ago
Select United flight, departing Thu, Nov 13 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, Nov 17, priced at $82 found 2 hours ago
Wed, Nov 19 - Wed, Nov 19
DEN
Denver Intl.
ORD
O'Hare Intl.
$84 Roundtrip, found 6 hours ago
$84
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Nov 19 from Denver Intl. to O'Hare Intl., returning Wed, Nov 19, priced at $84 found 6 hours ago
Wed, Nov 5 - Wed, Nov 12
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$84 Roundtrip, found 17 hours ago
$84
Roundtrip
found 17 hours ago
Select United flight, departing Wed, Nov 5 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Wed, Nov 12, priced at $84 found 17 hours ago
Sat, Oct 25 - Sat, Oct 25
TPA
Tampa Intl.
ORD
O'Hare Intl.
$87 Roundtrip, found 9 hours ago
$87
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Sat, Oct 25 from Tampa Intl. to O'Hare Intl., returning Sat, Oct 25, priced at $87 found 9 hours ago
Thu, Dec 18 - Wed, Dec 24
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$87 Roundtrip, just found
$87
Roundtrip
just found
Select Sun Country Airlines flight, departing Thu, Dec 18 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Wed, Dec 24, priced at $87 just found
Mon, Oct 27 - Thu, Oct 30
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$93 Roundtrip, found 18 hours ago
$93
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Mon, Oct 27 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Thu, Oct 30, priced at $93 found 18 hours ago
Thu, Nov 13 - Mon, Nov 17
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$97 Roundtrip, found 2 hours ago
$97
Roundtrip
found 2 hours ago
Select Delta flight, departing Thu, Nov 13 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, Nov 17, priced at $97 found 2 hours ago
Thu, Nov 13 - Thu, Nov 13
DEN
Denver Intl.
MDW
Midway Intl.
$104 Roundtrip, found 17 hours ago
$104
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Denver Intl. to Midway Intl., returning Thu, Nov 13, priced at $104 found 17 hours ago

Winnetka Flight Information

Traveling To
Winnetka
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Southwest Airlines, United, Spirit Airlines, Sun Country Airlines, Frontier Airlines, American Airlines, Delta
Flight Price
$77
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

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Winnetka economy flight packages

Price found within the past 48 hours. Click for updated prices.
The French Country Inn Lake Geneva
3.0-star property

The French Country Inn Lake Geneva

Nov 14 - Nov 16

2 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $477, price is now $295 per person
$295
per person
just found
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Oct 31 - Nov 2

2 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $824, price is now $473 per person
$473
per person
found 1 day ago
Level Chicago - River North
4.0-star property

Level Chicago - River North

Oct 31 - Nov 5

5 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,067, price is now $635 per person
$635
per person
found 1 day ago
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Winnetka premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Graduate by Hilton Evanston
4.0-star property

Graduate by Hilton Evanston

8.8/10 Excellent! (1,006 reviews)

Nov 21 - Nov 25

4 night stay

Miami (MIA) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,013, price is now $833 per person
$833
per person
found 1 day ago
We really like it here - it's a bit quirky, but it's very comfortable and the staff are great.

Reviewed on May 28, 2025

Level Chicago - River North
4.0-star property

Level Chicago - River North

9/10 Wonderful! (698 reviews)

Nov 21 - Nov 25

4 night stay

Miami (MIA) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,107, price is now $913 per person
$913
per person
found 1 day ago
The pool area is fantastic. Rooms very ample-sized and comfortable. I would stay here again!

Reviewed on Jul 8, 2024

Kimpton Gray Hotel by IHG
4.5-star property

Kimpton Gray Hotel by IHG

9.2/10 Wonderful! (1,007 reviews)

Nov 21 - Nov 25

4 night stay

Miami (MIA) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $989, price is now $877 per person
$877
per person
found 1 day ago
Soaking tub suite, spacious and very cozy. No worries on taking the ice bucket to the ice machine. Pre bagged ice for convince. Very cool.

Reviewed on Aug 18, 2025

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Winnetka first class flight packages

Price found within the past 48 hours. Click for updated prices.
Glenn Meadow Bed and Breakfast
4.0-star property

Glenn Meadow Bed and Breakfast

9.8/10 Exceptional! (79 reviews)

Nov 26 - Nov 29

3 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • FirstClass
Price was $1,348, price is now $1,298 per person
$1,298
per person
found 23 hours ago
I travel a lot and rarely leave reviews but wanted to take a minute to do so in this case. I highly recommend Glenn Meadow B&B. The price is reasonable, the home and location is very beautiful and peaceful, and the owner Tracey is a fantastic host who goes above and beyond. I accidentally left behind some expensive headphones and Tracey immediately shipped them back to me at no cost. On top of that she’s an excellent cook and breakfast was delicious. Can’t say enough good things about this place.

Reviewed on Sep 10, 2024

Victoria Resort and Bed & Breakfast
4.0-star property

Victoria Resort and Bed & Breakfast

9.4/10 Exceptional! (130 reviews)

Nov 26 - Nov 29

3 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • FirstClass
Price was $1,535, price is now $1,368 per person
$1,368
per person
found 23 hours ago
Elizabeth is a true gem of an employee! She’s a super chef, and a kind soul. She cared enough to prepare us kosher items. Her apple french toast and quiche were delicious. Our room was nice and the jacuzzi tub made for a great end to our days. Close to the beach and we used the resort bikes to go for a ride to the lighthouse. We were so impressed with Elizabeth’s hospitality that we talked our parents into coming and staying. We will be back. 10 out of 10 stars!! Treat yourself and enjoy the local wineries. Have Elizabeth prepare a charcuterie board for you and she’ll have it in the fridge in your room when you arrive, you won’t be sorry!

Reviewed on Oct 27, 2024

Old Harbor Inn
3.0-star property

Old Harbor Inn

9.4/10 Exceptional! (627 reviews)

Nov 26 - Nov 29

3 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • FirstClass
Price was $1,389, price is now $1,321 per person
$1,321
per person
found 23 hours ago
Clean, organized and beautiful views.

Reviewed on Jul 7, 2025

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Winnetka

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When flying with Orbitz, take advantage of frequent updates on your flights to Winnetka. Details and updates are sent to up to six contact numbers to ensure that you are kept abreast of the latest information on Winnetka flights. Frequent flyer and loyalty membership numbers may be updated within your Orbitz account profile.

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 $77 to $104. But it was jet-setters flying in from Minneapolis (MSP) 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.

More to Explore

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.