Cheap flights To Winfield (CHI) from $25

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Cheap Flights to Winfield from $25 One Way, $49 Round Trip

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

Wed, Oct 22 - Wed, Oct 29
LGA
LaGuardia
ORD
O'Hare Intl.
$49 Roundtrip, just found
$49
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Oct 22 from LaGuardia to O'Hare Intl., returning Wed, Oct 29, priced at $49 just found
Tue, Nov 18 - Tue, Nov 18
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$81 Roundtrip, just found
$81
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Nov 18 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Nov 18, priced at $81 just found
Tue, Nov 4 - Tue, Nov 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$81 Roundtrip, found 4 hours ago
$81
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Nov 4 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Nov 11, priced at $81 found 4 hours ago
Wed, Nov 5 - Wed, Nov 5
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$84 Roundtrip, found 2 hours ago
$84
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Nov 5 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Nov 5, priced at $84 found 2 hours ago
Wed, Nov 5 - Wed, Nov 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$84 Roundtrip, found 2 hours ago
$84
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Nov 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Nov 5, priced at $84 found 2 hours ago
Tue, Dec 16 - Tue, Jan 6
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$88 Roundtrip, found 12 hours ago
$88
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Tue, Dec 16 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Jan 6, priced at $88 found 12 hours ago
Sat, Oct 18 - Sat, Oct 25
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$90 Roundtrip, found 4 hours ago
$90
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Oct 18 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Oct 25, priced at $90 found 4 hours ago
Wed, Feb 18 - Wed, Feb 25
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$90 Roundtrip, found 5 days ago
$90
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Feb 18 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, Feb 25, priced at $90 found 5 days ago
Wed, Oct 29 - Wed, Oct 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 4 days ago
$134
Roundtrip
found 4 days ago
Select United flight, departing Wed, Oct 29 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Oct 29, priced at $134 found 4 days ago
Sat, Dec 6 - Tue, Dec 9
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$137 Roundtrip, found 6 days ago
$137
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Dec 6 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Dec 9, priced at $137 found 6 days ago

Winfield Flight Information

Traveling To
Winfield
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Spirit Airlines, Frontier Airlines, Southwest Airlines, American Airlines, United
Flight Price
$49
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

Winfield 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 $426, price is now $275 per person
$275
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
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Nov 14 - Nov 16

2 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $532, price is now $324 per person
$324
per person
found 1 day ago
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Winfield 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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Winfield 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 14 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 14 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 14 hours ago
Clean, organized and beautiful views.

Reviewed on Jul 7, 2025

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Winfield

Orbitz uses cutting edge mobile technology to help get you the best deals on Winfield flights. We offer guaranteed low prices on air tickets that can be combined with hotels and car rentals to save you even more money.

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Discount flights to Winfield can be combined with car rental to get you additional savings. Just use our Flight Matrix to see how your budget air ticket can be combined with a car rental to make your trip not only inexpensive but also more convenient.

Use Multiple Airlines To Ensure You Get The Best Deal

Orbitz allows you to use multiple airlines for flights to Winfield. By using a combination of airlines for discount flights you are guaranteed to get the lowest fares each way and get the schedule that is most convenient for you.

Store Your Frequent Flyer Information on Orbitz For Easy Access

Booking with Orbitz will still allow you to apply miles for flights to Winfield to your frequent flyer program. Not only that, but your frequent flyer information will be safely stored on our website, so it will be easy to access the next time you book a discount air ticket with Orbitz.

Frequently asked questions

Which airlines fly to Winfield?
With 20 airlines to select from, finding a flight to suit your budget and travel dates will be a piece of cake. O'Hare Intl. Airport (ORD) is a major gateway to Winfield and where you're likely to be landing. These leading international carriers will get you there:

  • United Airlines - 612 flights to Winfield per month
  • American Airlines - 339 flights to Winfield per month
  • Air Canada - 190 flights to Winfield per month

What is the best airport to fly to in Winfield?
Reserve a flight to O'Hare Intl. Airport (ORD) and get ready to explore the sights of this unique city. The airport is around 15 miles northeast of the downtown area. Also take a look at the price of flights to Midway Intl. Airport (MDW), which is another entry point for Winfield.
How much is a flight to Winfield?
Travelers from far and wide picked up round-trip bargains ranging from $49 to $137 this week to Winfield. Flying in from New York (LGA)? The cheapest one-way tickets started at just $25.
How to book the cheapest flight to Winfield?
Using Orbitz, you'll uncover some of the most incredible flight deals around from a big range of airlines. But if you'd like to improve your chances of landing cheap flights to Winfield, here are a few pointers to get started:

  • Consider other airports for a better deal. Enter your preferred departure and arrival points in the form fields, then click on the 'Nearby airports' function below. It will list the available options.
  • If your travel plans aren't set in concrete, click on the 'Show flexible dates' link to compare flight deals across different departure dates. Go with any suitable cheaper fare that pops up.
  • Select 'Show options' to narrow down your search results. You can pick your preferred seating class and airline here. Under 'Sort & Filter' to the left, you can even specify whether you want to fly in the morning, afternoon or evening.
  • The early bird gets the best savings, so book your tickets the moment you know your travel dates. The most affordable fares sell out quickly and prices rise as the departure date nears.
  • Make big savings on your adventure by combining your hotel, flights and car rentals into one convenient package deal. Your budget will thank you for it.
  • Don't fly during peak seasons if you can. By avoiding summer and school vacations, you can save loads on your airfare.

How long is a flight to Winfield?
You could have time to read a couple of chapters of a novel, or you might get through the whole thing! Flight times depend on where you're taking off from, but these busy routes to Winfield will offer some insight:

  • 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 Winfield?
Generally speaking, January is the best month to purchase your airfare. This is closely followed by February and August. Keep this in mind while searching for a cheap flight to Winfield.
What day of the week is the cheapest to book a flight to Winfield?
Typically, Tuesdays, Wednesdays and Saturdays are the cheapest days of the week to book flights to Winfield. If you're after the most competitive airfares, search across those days and you're likely to land yourself an incredible flight deal.
What is the cheapest day of the week to fly to Winfield?
Consider leaving early in the week to nab cheap flights to Winfield. Orbitz data from 2020 suggests Monday is generally the most affordable day to start your trip, followed by Tuesday. Saturdays were shown to have the most expensive ticket fares. This is probably because most travelers prefer to kick off their break when the weekend rolls around.
What is the cheapest month to fly to Winfield?
To pick up cheap flights to Winfield, you should leave in August. If getting a great deal on your ticket is your number one priority, Orbitz data has found that this is generally the best month to go on a trip. June is when fares are the most expensive.
Which airlines allow free cancellation?
If you're worried your travel plans could change, Orbitz can help you lock in a flexible ticket. All you need to do is click on "Filter by flexible change policies" when searching for your Winfield flights. We'll show you carriers that include free cancellation and no change fees — all on top of irresistibly low prices.
What do I need for the flight to Winfield?
There's nothing more enjoyable than jetting somewhere new, but it's smart to be prepared. The following practical tips will help get your journey started on the right foot:

  • Your travel documents are the most important things you'll need to take with you on your flight. To avoid any confusion at check-in time, make sure that the name on your ticket corresponds with your government-issued photo ID.
  • To keep you amused on your short trip to Winfield, download your favorite tunes or stock up the audiobook library on your phone. Food can also be a good distraction while in the air, so maybe even bring some light snacks.
  • Whatever the temperature is doing outside, plane cabins can get chilly. Take a hoodie on board to keep yourself cozy.

How many direct flights are there to Winfield?
Your amazing adventure is just one easy plane ride away, with 2,332 direct flights to Winfield every month. Search for your fare with Orbitz and lock in a fantastic deal with United Airlines, American Airlines or Delta Air Lines. Other reputable carriers that provide nonstop services include Southwest Airlines, Spirit Airlines and Air Canada.
How do I get cheap first-class/business deals to Winfield?
If you think a business or first-class airfare is way out of your reach, think again. Here are just a few tips to help you nab a premium flight to Winfield for less:

  • Be flexible with your travel dates and wait for exclusive offers or sales on first or business-class airfares.
  • Search for a budget carrier that has business-class seats. They usually come with more space and a glass of bubbly — but without the premium price.
  • Take advantage of your airline's loyalty scheme and upgrade your seat. Alternatively, you can try bidding for an upgrade in an online auction if available.

How to get into Winfield from the airport?
Step off the tarmac at O'Hare Intl. Airport (ORD) and then pick up the keys from one of the O'Hare Intl. Airport (ORD) car rental suppliers on-site, Thrifty Car Rental or Dollar. With your own set of wheels, making your way to the downtown area of Winfield from ORD will be a cinch. All you need to do is set your GPS and cruise 15 miles to the southwest. Alternatively, you could take a taxi or public transportation into town and rent a car directly from the city center. Check out what's available on our Winfield car rentals.
Travel tips for Winfield

  • Lace up your comfy kicks and tour this lively city on foot. There are many awesome attractions to take in, such as French Market and Dupage County Historical Museum.
  • If you're in the mood for an easy day trip, there are more sights waiting for you a short commute from the hustle and bustle. Find out why Wrigley Field and McCormick Place are on the must-do lists of most Winfield adventurers.
  • Want to see what else Chicago has to offer? Pick up a car rental and hit the road to Gurnee or Waukegan. With your own ride, getting to those off-radar destinations will also be a snap.

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.