Cheap flights To Winfield (CHI) from $49

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Cheap Flights to Winfield from $49 One Way, $78 Round Trip

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

Thu, Oct 22 - Wed, Oct 28
DEN
Denver Intl.
ORD
O'Hare Intl.
$78 Roundtrip, found 6 days ago
$78
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Oct 22 from Denver Intl. to O'Hare Intl., returning Wed, Oct 28, priced at $78 found 6 days ago
Fri, Nov 6 - Wed, Nov 11
SFB
Orlando Sanford Intl.
RFD
Greater Rockford
$90 Roundtrip, found 6 days ago
$90
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Fri, Nov 6 from Orlando Sanford Intl. to Greater Rockford, returning Wed, Nov 11, priced at $90 found 6 days ago
Thu, Dec 3 - Thu, Dec 10
DEN
Denver Intl.
ORD
O'Hare Intl.
$98 Roundtrip, found 6 days ago
$98
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Dec 3 from Denver Intl. to O'Hare Intl., returning Thu, Dec 10, priced at $98 found 6 days ago
Sat, Jan 23 - Sat, Jan 30
DEN
Denver Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jan 23 from Denver Intl. to O'Hare Intl., returning Sat, Jan 30, priced at $100 found 1 day ago
Sat, Oct 31 - Sat, Nov 7
DEN
Denver Intl.
ORD
O'Hare Intl.
$102 Roundtrip, found 2 days ago
$102
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Oct 31 from Denver Intl. to O'Hare Intl., returning Sat, Nov 7, priced at $102 found 2 days ago
Sat, Oct 24 - Wed, Oct 28
DEN
Denver Intl.
ORD
O'Hare Intl.
$104 Roundtrip, found 6 days ago
$104
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Oct 24 from Denver Intl. to O'Hare Intl., returning Wed, Oct 28, priced at $104 found 6 days ago
Thu, Jan 21 - Sun, Jan 24
PGD
Punta Gorda Airport
MDW
Midway Intl.
$113 Roundtrip, found 6 days ago
$113
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Thu, Jan 21 from Punta Gorda Airport to Midway Intl., returning Sun, Jan 24, priced at $113 found 6 days ago
Sat, Oct 17 - Sun, Oct 25
PGD
Punta Gorda Airport
RFD
Greater Rockford
$173 Roundtrip, found 6 days ago
$173
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Sat, Oct 17 from Punta Gorda Airport to Greater Rockford, returning Sun, Oct 25, priced at $173 found 6 days ago
Mon, Oct 26 - Thu, Oct 29
DEN
Denver Intl.
MDW
Midway Intl.
$179 Roundtrip, found 5 days ago
$179
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Oct 26 from Denver Intl. to Midway Intl., returning Thu, Oct 29, priced at $179 found 5 days ago
Mon, Oct 19 - Wed, Oct 21
CLT
Charlotte-Douglas Intl.
ORD
O'Hare Intl.
$195 Roundtrip, found 4 days ago
$195
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Oct 19 from Charlotte-Douglas Intl. to O'Hare Intl., returning Wed, Oct 21, priced at $195 found 4 days ago

Winfield Flight Information

Traveling To
Winfield
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Allegiant Air
Flight Price
$78
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Winfield economy flight packages

Price found within the past 48 hours. Click for updated prices.
Villa Christina
3.0-star property

Villa Christina

Oct 23 - Oct 28

5 night stay

Los Angeles (LAX) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,258, price is now $867 per person
$867
per person
found 1 day ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Nov 5 - Nov 8

3 night stay

Austin (AUS) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Austin (AUS)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,610, price is now $1,096 per person
$1,096
per person
found 1 day ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Nov 5 - Nov 8

3 night stay

Austin (AUS) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Austin (AUS)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,264, price is now $886 per person
$886
per person
found 1 day ago
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See all available trips from Los Angeles to Winfield
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Winfield first class flight packages

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

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (5,174 reviews)

Nov 13 - Nov 16

3 night stay

Houston (IAH) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,392, price is now $1,075 per person
$1,075
per person
found 1 day ago
Only the wall outlet near the beds didn't work ...just that...everything was great !! Excelent hotel

Reviewed on Sep 21, 2026

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.6/10 Exceptional! (1,995 reviews)

Nov 13 - Nov 16

3 night stay

Houston (IAH) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,701, price is now $1,270 per person
$1,270
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

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 1 day ago

Don't see what you're looking for?
See all available trips from Houston to Winfield
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Winfield

Get the absolute lowest prices on flights to Winfield 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.

Book Your Flight To Winfield Using Your Mobile Device

New mobile app tools enable those with hand-held devices to scout out the best bargains and to secure tickets from any location. If you have an iPhone, iPad or Android device, you may take advantage of special discounts, only available to mobile device customers, when you book hotel rooms or car rentals on the same day as booking Winfield flights.

Avoid Check-In Hassles When Traveling On Flights to Winfield

Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Winfield 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 Winfield flight using 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 $78 to $195 this week to Winfield. Flying in from Denver (DEN)? The cheapest one-way tickets started at just $49.
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.