Cheap flights To Winfield (CHI) from $54

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Cheap Flights to Winfield from $54 One Way, $90 Round Trip

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

Tue, Oct 27 - Wed, Oct 28
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$90 Roundtrip, found 6 days ago
$90
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Oct 27 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Oct 28, priced at $90 found 6 days ago
Tue, Oct 6 - Tue, Oct 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Oct 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Oct 6, priced at $100 found 1 day ago
Wed, Oct 7 - Tue, Oct 13
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$102 Roundtrip, found 5 days ago
$102
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Oct 7 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Oct 13, priced at $102 found 5 days ago
Tue, Oct 20 - Sat, Nov 7
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Tue, Oct 20 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Nov 7, priced at $117 found 5 days ago
Thu, Feb 18 - Wed, Feb 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$136 Roundtrip, just found
$136
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Feb 18 from Los Angeles Intl. to O'Hare Intl., returning Wed, Feb 24, priced at $136 just found
Tue, Nov 17 - Tue, Nov 17
LGA
LaGuardia
ORD
O'Hare Intl.
$164 Roundtrip, found 2 days ago
$164
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Nov 17 from LaGuardia to O'Hare Intl., returning Tue, Nov 17, priced at $164 found 2 days ago
Wed, Oct 7 - Wed, Oct 14
LGA
LaGuardia
MDW
Midway Intl.
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Oct 7 from LaGuardia to Midway Intl., returning Wed, Oct 14, priced at $167 found 2 days ago
Tue, Nov 3 - Wed, Nov 4
LGA
LaGuardia
ORD
O'Hare Intl.
$183 Roundtrip, found 3 days ago
$183
Roundtrip
found 3 days ago
Select United flight, departing Tue, Nov 3 from LaGuardia to O'Hare Intl., returning Wed, Nov 4, priced at $183 found 3 days ago
Sat, Oct 17 - Sat, Oct 24
LGA
LaGuardia
ORD
O'Hare Intl.
$183 Roundtrip, found 4 days ago
$183
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Oct 17 from LaGuardia to O'Hare Intl., returning Sat, Oct 24, priced at $183 found 4 days ago
Wed, Oct 21 - Sat, Oct 24
LGA
LaGuardia
MDW
Midway Intl.
$186 Roundtrip, found 4 days ago
$186
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Oct 21 from LaGuardia to Midway Intl., returning Sat, Oct 24, priced at $186 found 4 days ago

Winfield Flight Information

Traveling To
Winfield
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Southwest Airlines, United, Delta
Flight Price
$90
Earliest Departing Flight
Latest Departing Flight

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Winfield economy flight packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

Oct 28 - Oct 31

3 night stay

Denver (DEN) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $949, price is now $571 per person
$571
per person
found 20 hours ago
Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

Oct 22 - Oct 26

4 night stay

Denver (DEN) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,217, price is now $702 per person
$702
per person
found 1 day ago
Swissotel - Chicago
4.5-star property

Swissotel - Chicago

Oct 22 - Oct 26

4 night stay

Denver (DEN) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,159, price is now $674 per person
$674
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.
The Talbott, Autograph Collection
4.5-star property

The Talbott, Autograph Collection

9.4/10 Exceptional! (165 reviews)

Nov 6 - Nov 10

4 night stay

Houston (IAH) to Chicago (ORD)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,111, price is now $786 per person
$786
per person
found 1 day ago

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (5,174 reviews)

Nov 6 - Nov 10

4 night stay

Houston (IAH) to Chicago (ORD)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,478, price is now $979 per person
$979
per person
found 1 day ago
Friendly and warm

Reviewed on Sep 20, 2026

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.6/10 Exceptional! (1,995 reviews)

Nov 6 - Nov 10

4 night stay

Houston (IAH) to Chicago (ORD)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,957, price is now $1,299 per person
$1,299
per person
found 1 day ago
Always great service and hospitality here. Rooms are spotless and attended to multiple times daily.

Reviewed on Sep 20, 2026

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Winfield first class flight packages

Price found within the past 48 hours. Click for updated prices.
Thompson Chicago, by Hyatt
4.5-star property

Thompson Chicago, by Hyatt

9.2/10 Wonderful! (1,409 reviews)

Nov 13 - Nov 16

3 night stay

Houston (IAH) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,044, price is now $883 per person
$883
per person
found 15 hours ago
Great hotel

Reviewed on Sep 19, 2026

Swissotel - Chicago
4.5-star property

Swissotel - Chicago

9/10 Wonderful! (3,512 reviews)

Nov 13 - Nov 16

3 night stay

Houston (IAH) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,531, price is now $1,129 per person
$1,129
per person
found 15 hours ago

Pendry Chicago
4.5-star property

Pendry Chicago

9.2/10 Wonderful! (1,146 reviews)

Nov 13 - Nov 16

3 night stay

Houston (IAH) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,415, price is now $1,150 per person
$1,150
per person
found 15 hours ago

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Winfield

If you are looking for discount prices on flights to Winfield then look no further than Orbitz. With some of the best deals available, cutting-edge technology, and great customer service, Orbitz makes booking Winfield flights easy and affordable.

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The Complete Package

Orbitz makes it stress-free to book Winfield flights, and we can also help you figure out the rest of your trip just as easily. If you need great deals on hotels and car rentals following your flights to Winfield, just add the details to your booking and search for the cheapest deals out there. And why waste time lining up for admission to attractions and events? With Orbitz, you can book tickets in advance and waltz straight in.

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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 $90 to $186 this week to Winfield. Flying in from Atlanta (ATL)? The cheapest one-way tickets started at just $54.
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

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.