Cheap flights To Winfield (CHI) from $36

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Cheap Flights to Winfield from $36 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 2 days ago
$60
Roundtrip
found 2 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 2 days ago
Mon, Oct 20 - Thu, Oct 23
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$70 Roundtrip, found 4 days ago
$70
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Oct 20 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Thu, Oct 23, priced at $70 found 4 days ago
Tue, Oct 7 - Tue, Oct 14
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$70 Roundtrip, found 4 days ago
$70
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Oct 7 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, Oct 14, priced at $70 found 4 days ago
Wed, Oct 8 - Tue, Oct 14
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$70 Roundtrip, found 3 days ago
$70
Roundtrip
found 3 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 3 days ago
Wed, Aug 13 - Wed, Aug 20
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 1 hour ago
$73
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, Aug 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Aug 20, priced at $73 found 1 hour ago
Mon, Sep 29 - Sun, Oct 19
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$75 Roundtrip, found 4 days ago
$75
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Sep 29 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Sun, Oct 19, priced at $75 found 4 days ago
Thu, Sep 18 - Thu, Sep 18
PHL
Philadelphia Intl.
MDW
Midway Intl.
$78 Roundtrip, found 5 days ago
$78
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Sep 18 from Philadelphia Intl. to Midway Intl., returning Thu, Sep 18, priced at $78 found 5 days ago
Wed, Nov 5 - Tue, Nov 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$85 Roundtrip, just found
$85
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Nov 5 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Nov 11, priced at $85 just found
Mon, Sep 15 - Mon, Oct 6
PHL
Philadelphia Intl.
ORD
O'Hare Intl.
$95 Roundtrip, found 4 days ago
$95
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Sep 15 from Philadelphia Intl. to O'Hare Intl., returning Mon, Oct 6, priced at $95 found 4 days ago
Sat, Dec 13 - Sat, Dec 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 3 days ago
$134
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Dec 13 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Dec 13, priced at $134 found 3 days ago

Winfield Flight Information

Traveling To
Winfield
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Spirit Airlines, Frontier Airlines, Southwest Airlines, Delta, 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

Winfield economy flight packages

Price found within the past 48 hours. Click for updated prices.
Wingate by Wyndham - Joliet
2.5-star property

Wingate by Wyndham - Joliet

Sep 20 - Sep 25

5 night stay

Houston (HOU) to Chicago (CHI)

Spirit Airlines • 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 20 - Sep 25

5 night stay

Houston (HOU) to Chicago (CHI)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 hour ago
La Banque Hotel
4.0-star property

La Banque Hotel

Aug 29 - Sep 1

3 night stay

Minneapolis (MSP) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 3 hours ago
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Winfield first class flight packages

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

Hilton Chicago

8.4/10 Very Good! (1,986 reviews)

Aug 29 - Sep 1

3 night stay

Minneapolis (MSP) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
per person
found 8 hours ago
Good facility with convenient location.

Reviewed on Jul 27, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,635 reviews)

Sep 17 - Sep 19

2 night stay

Atlanta (ATL) to Chicago (ORD)

Delta • Roundtrip • FirstClass
per person
found 23 hours ago
This is the nicest hotel that I have ever stayed at. Everything was perfect!

Reviewed on Jun 16, 2025

Nobu Hotel Chicago
5.0-star property

Nobu Hotel Chicago

9.4/10 Exceptional! (689 reviews)

Aug 29 - Sep 1

3 night stay

Minneapolis (MSP) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
per person
found 8 hours ago
Best hotel I ever been in

Reviewed on Jul 16, 2024

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See all available trips from Minneapolis to Winfield
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Winfield

Finding cheap flights to Winfield is easy when you have Orbitz at your fingertips. Not only does Orbitz offer great deals on Winfield flights, but we also include some special extras to make booking a breeze. Just check out our:

Mobile Site and Apps

With Orbitz’s mobile site, m.orbitz.com, you can book your flights to Winfield through your smartphone or tablet’s Web browser. Plus, our free downloadable apps for Android and iPhone mean it’s just a simple click to access your flight updates and alerts. You can even book exclusive mobile-only deals on hotels to go with your flights to Winfield—even on the same day.

Pick and Choose or Book Full Vacation Packages

Don’t just be satisfied with great deals on Winfield flights—go for the full package! With Orbitz, you can also find fantastic savings on the perfect hotel, car rental, cruise, and even activities, so you don’t waste your trip waiting in line but have the time to enjoy your trip. Pick and choose the add-ons you need, or book an entire vacation package for greater overall discounts.

Rewards That Are Miles Better

Booking directly with an airline earns you air miles or points, and you can get those same rewards with booking on Orbitz too. When you book qualifying flights to Winfield with Orbitz, just add in your frequent flyer number during your online booking and your details will be sent to your program.

Great Deals Every Day

Add in our extra savings on packages, free nights, and other discounts, and you know you are in good hands.

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 $60 to $134 this week to Winfield. Flying in from Atlanta (ATL)? The cheapest one-way tickets started at just $36.
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.

Nearby

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.