Cheap flights To Winfield (CHI) from $74

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Cheap Flights to Winfield from $74 One Way, $148 Round Trip

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

Sat, Sep 12 - Sat, Sep 19
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$148 Roundtrip, found 7 hours ago
$148
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Sep 12 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Sep 19, priced at $148 found 7 hours ago
Wed, Sep 9 - Wed, Sep 16
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$148 Roundtrip, found 5 hours ago
$148
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Wed, Sep 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Sep 16, priced at $148 found 5 hours ago
Wed, Aug 12 - Sat, Aug 15
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$152 Roundtrip, just found
$152
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Aug 12 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Aug 15, priced at $152 just found
Sat, Sep 5 - Tue, Sep 8
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 3 hours ago
$153
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Sep 5 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $153 found 3 hours ago
Tue, Sep 22 - Tue, Sep 22
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$166 Roundtrip, found 2 hours ago
$166
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Tue, Sep 22 from John F. Kennedy Intl. to O'Hare Intl., returning Tue, Sep 22, priced at $166 found 2 hours ago
Tue, Sep 8 - Wed, Sep 9
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$170 Roundtrip, found 3 hours ago
$170
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Tue, Sep 8 from Newark Liberty Intl. Airport to Greater Rockford, returning Wed, Sep 9, priced at $170 found 3 hours ago
Wed, Sep 2 - Tue, Sep 8
LGA
LaGuardia
RFD
Greater Rockford
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Sep 2 from LaGuardia to Greater Rockford, returning Tue, Sep 8, priced at $170 found 1 day ago
Sat, Jul 25 - Wed, Jul 29
JFK
John F. Kennedy Intl.
RFD
Greater Rockford
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jul 25 from John F. Kennedy Intl. to Greater Rockford, returning Wed, Jul 29, priced at $170 found 1 day ago
Wed, Sep 16 - Sat, Sep 19
LGA
LaGuardia
MDW
Midway Intl.
$171 Roundtrip, found 11 hours ago
$171
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Wed, Sep 16 from LaGuardia to Midway Intl., returning Sat, Sep 19, priced at $171 found 11 hours ago
Wed, Oct 7 - Sat, Oct 24
LGA
LaGuardia
ORD
O'Hare Intl.
$171 Roundtrip, just found
$171
Roundtrip
just found
Select United flight, departing Wed, Oct 7 from LaGuardia to O'Hare Intl., returning Sat, Oct 24, priced at $171 just found

Winfield Flight Information

Traveling To
Winfield
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Southwest Airlines, JetBlue Airways, American Airlines, United
Flight Price
$148
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.
Omni Chicago Hotel
4.5-star property

Omni Chicago Hotel

Aug 3 - Aug 6

3 night stay

Denver (DEN) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Denver (DEN)

Frontier Airlines • Coach
Save 100% on your flight
Price was $937, price is now $667 per person
$667
per person
found 1 day ago
Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

Aug 2 - Aug 7

5 night stay

Denver (DEN) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Denver (DEN)

Frontier Airlines • Coach
Save 100% on your flight
Price was $3,255, price is now $2,053 per person
$2,053
per person
found 1 day ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Aug 3 - Aug 6

3 night stay

Denver (DEN) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Denver (DEN)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,004, price is now $688 per person
$688
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.
Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

9.2/10 Wonderful! (504 reviews)

Aug 7 - Aug 9

2 night stay

San Francisco (SFO) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,011, price is now $881 per person
$881
per person
found 7 hours ago
The staff was extremely friendly and flexible regarding scheduling; this place is amazing.

Reviewed on Jul 1, 2026

Staypineapple, An Iconic Hotel, The Loop
4.0-star property

Staypineapple, An Iconic Hotel, The Loop

9.4/10 Exceptional! (1,109 reviews)

Aug 2 - Aug 6

4 night stay

Denver (DEN) to Chicago (ORD)

Frontier Airlines • Roundtrip • PremiumEconomy
Price was $1,214, price is now $1,080 per person
$1,080
per person
found 1 day ago
La atención hacia mi mascota y detalles en el cuarto fue increíble, Lo único que en recepción deberían de tener a alguien que hable inglés y español, Para poder hacer preguntas y dudas que uno pueda tener ,Por lo demás el señor del vallet parking fue muy amable y hablaba español nos aclaro bastantes dudas ,En general si me volvería a ospedar sin duda alguna .

Reviewed on Jul 2, 2026

The Peninsula Chicago
5.0-star property

The Peninsula Chicago

9.8/10 Exceptional! (1,003 reviews)

Aug 7 - Aug 9

2 night stay

San Francisco (SFO) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,632, price is now $1,296 per person
$1,296
per person
found 7 hours ago
Fantastic!

Reviewed on Jul 1, 2026

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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! (4,518 reviews)

Aug 2 - Aug 6

4 night stay

Denver (DEN) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,769, price is now $1,328 per person
$1,328
per person
found 1 day ago
The male receptionist was extremely helpful, friendly, and welcoming. Unfortunately, the female receptionist was not as helpful or friendly. Her coworker noticed that I wasn't receiving the assistance I needed and stepped in to help, which I really appreciated. I've stayed at several RIU hotels before and have always been able to check in early when a room was available. This was the first time I've experienced a significant delay with check-in. Overall, I had a great stay. The hotel is in an excellent location, with everything within walking distance, making it very convenient to explore the area. Breakfast is included, which is a nice benefit, but the quality could be improved. The selection was very basic and limited compared to what I've experienced at other RIU hotels.

Reviewed on Jul 2, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,554 reviews)

Aug 1 - Aug 8

7 night stay

New York (LGA) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,628, price is now $1,849 per person
$1,849
per person
found 17 hours ago
Excellente

Reviewed on Jul 1, 2026

LondonHouse Chicago, Curio Collection by Hilton
4.5-star property

LondonHouse Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (3,756 reviews)

Aug 1 - Aug 8

7 night stay

New York (LGA) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,766, price is now $1,952 per person
$1,952
per person
found 17 hours ago
An amazing hotel with an amazing river view! I will definitely be staying there again!

Reviewed on Jul 1, 2026

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Winfield

Start your search for cheap flights to Winfield on Orbitz. Orbitz is where you will discover guaranteed low prices on Winfield flights, as well as all of the following conveniences:

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Low Prices Guaranteed on Flights to Winfield

Orbitz offers large discounts on a wide range of Winfield flights. Through our easy-to-use site, you can find, plan, and reserve your desired flights to Winfield while taking advantage of the lowest fares around.

Customer Care When You Need It

Orbitz is dedicated to making your flight booking experience as stress-free as possible. If you need to cancel your reservation, you can do so at your own convenience by going to the Orbitz website. If you need to change your flights to Winfield to another time or date, you can contact our customer service representatives by phone, and they help you make the flight adjustments you need.

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Orbitz lets you add your loyalty or frequent flyer account numbers when you book qualifying flights to Winfield. So don’t worry about missing out on earning miles or points simply because you aren’t booking with the airline directly. You can save on your flights, and rack up miles too.

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 $148 to $171 this week to Winfield. Flying in from Dallas (DFW)? The cheapest one-way tickets started at just $74.
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.