HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$46+ Cheap flights from Chicago Midway Airport

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — DFW
Dec 21 — Dec 281
Sun 12/21
Sun 12/28
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

What to know about flights from Midway

Discover essential information about flights departing from Midway, including flight schedules, destinations, airlines operating at the Midway airport, and any specific guidelines or requirements for travelers. Please note that the information is based on the most recent updates available. Data last updated November 21, 2025.

Cheapest airline

Emirates

Good round-trip deal

$88 or less

Good one-way deal

$48 or less
On average, Emirates currently has the cheapest one-way flight from Chicago Midway (avg. price of $1,156).
Search Deals
Price to beat on a round-trip flight from Chicago Midway.
Search Deals
Price to beat on a one-way flight from Chicago Midway.
Search Deals

Find flights from Midway

Cheapest flights from Midway
Explore the most affordable flight options available from Midway. Find the lowest fares based on data from user searches, with prices last updated on November 21, 2025.

This CheapOair deal was found by Cheapflights users on 11/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/1610:10 amMDW - DFW
Nonstop2h 45mFrontier
Sun 1/183:00 pmDFW - MDW
Nonstop2h 20mFrontier
Deal found 11/21$90
This CheapOair deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/99:15 amMDW - DFW
Nonstop2h 50mFrontier
Mon 1/121:15 pmDFW - MDW
Nonstop2h 18mFrontier
Deal found 11/20$91
This Super.com deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/48:05 amMDW - DFW
Nonstop2h 42mFrontier
Thu 12/1111:47 amDFW - MDW
Nonstop2h 17mFrontier
Deal found 11/20$94
This CheapOair deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/78:05 amMDW - DFW
Nonstop2h 42mFrontier
Mon 12/89:02 amDFW - MDW
Nonstop2h 18mFrontier
Deal found 11/18$95
This WAYA deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/53:10 pmMDW - MCO
Nonstop2h 48mMultiple Airlines
Mon 1/121:53 pmMCO - MDW
1 stop9h 24mMultiple Airlines
Deal found 11/19$96
This Super.com deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:05 amMDW - DFW
Nonstop2h 42mFrontier
Sun 12/1411:47 amDFW - MDW
Nonstop2h 17mFrontier
Deal found 11/18$97
This WAYA deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/66:10 amMDW - MCO
1 stop5h 40mMultiple Airlines
Fri 1/99:03 pmMCO - MDW
Nonstop2h 56mMultiple Airlines
Deal found 11/20$97
This CheapOair deal was found by Cheapflights users on 11/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/198:00 amMDW - DFW
Nonstop2h 42mFrontier
Sun 12/2111:42 amDFW - MDW
Nonstop2h 17mFrontier
Deal found 11/20$98
This Frontier deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/56:12 amMDW - MCO
1 stop9h 38mFrontier
Fri 1/99:03 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 11/19$98
This WAYA deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/113:10 pmMDW - MCO
Nonstop2h 48mMultiple Airlines
Fri 12/126:14 pmMCO - MDW
1 stop4h 58mMultiple Airlines
Deal found 11/19$99
This Kiwi.com deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/1311:39 amMDW - DFW
1 stop11h 14mFrontier
Thu 1/153:00 pmDFW - MDW
Nonstop2h 20mFrontier
Deal found 11/19$100
This Kiwi.com deal was found by Cheapflights users on 11/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/96:10 amMDW - MCO
1 stop17h 11mFrontier
Sun 1/119:03 pmMCO - MDW
Nonstop2h 56mFrontier
Deal found 11/21$100

Find flights from Midway within your budget

 
Find flights departing from Midway that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on November 21, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Dallas/Fort Worth

Route

Depart

Return

Price

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Fri 12/19

8:00 am-10:42 am

Nonstop2h 42m

Dallas/Fort Worth

Sat 12/27

1:10 pm-3:28 pm

Nonstop2h 18m

$117

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 12/18

6:12 am-8:23 pm

1 stop13h 11m

Miami

Wed 12/24

9:05 pm-5:38 pm

1 stop21h 33m

$130

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Sun 12/21

8:00 am-10:42 am

Nonstop2h 42m

Dallas/Fort Worth

Mon 12/29

10:45 am-10:12 pm

1 stop11h 27m

$136

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 1/1

5:05 am-8:40 am

Nonstop2h 35m

Orlando

Thu 1/8

7:05 pm-9:00 pm

Nonstop2h 55m

$137

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 1/7

3:15 pm-6:50 pm

Nonstop2h 35m

Orlando

Fri 1/9

7:05 pm-9:00 pm

Nonstop2h 55m

$137

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 1/12

6:05 am-9:10 am

Nonstop2h 05m

New York LaGuardia

Thu 1/15

6:00 am-7:40 am

Nonstop2h 40m

$139

ChicagoLas Vegas

MDW - LAS

MDWLAS

Chicago Midway

Wed 2/18

6:00 am-10:00 am

1 stop6h 00m

Las Vegas Harry Reid Intl

Sat 2/21

11:40 pm-5:05 am

Nonstop3h 25m

$141

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Fri 12/19

8:00 am-10:42 am

Nonstop2h 42m

Dallas/Fort Worth

Mon 12/29

10:45 am-10:12 pm

1 stop11h 27m

$146

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 2/3

6:50 am-1:30 pm

1 stop5h 40m

Orlando

Wed 2/11

4:45 pm-6:40 pm

Nonstop2h 55m

$147

ChicagoLas Vegas

MDW - LAS

MDWLAS

Chicago Midway

Tue 1/6

7:50 pm-9:55 pm

Nonstop4h 05m

Las Vegas Harry Reid Intl

Fri 1/9

11:40 pm-5:05 am

Nonstop3h 25m

$154

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 60 results
1
2
3
...
6

Compare providers for flights from Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway in November
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapOairPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
MytripPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: Among all the travel providers offering deals on flights from Chicago Midway Airport, CheapOair has been found to have the most accurate pricing. Users can find the same prices on deals on Cheapflights as CheapOair about >95% of the time. This is based on searches for flights from Chicago Midway Airport made on Cheapflights over the past month and is updated monthly.
  • Most trusted provider: In terms of trustworthiness, Cheapflights users rate CheapOair the highest out of those offering flight deals from Chicago Midway Airport. CheapOair has a user feedback rating of 3 out of 3 stars (3 being the best) and has received the most positive sentiment from Cheapflights users searching for flights from Chicago Midway Airport. This info is gathered from Cheapflights searches over the past month.

Midway travel tips

Get helpful tips and advice for traveling to or from Midway. Find recommendations for transportation, accommodations, local attractions, dining options, and other practical tips to enhance your travel experience. Please note that the travel tips are based on general knowledge and recommendations. Data last updated November 21, 2025.
  • When traveling through the Chicago Midway International Airport (MDW), note that the security checkpoint offers three different lanes for your convenience: a business/experienced traveler lane, a lane for casual travelers, and a family lane for travelers with children who may need additional time to go at their own pace.
  • Travelers to Chicago Midway International Airport (MDW) in need of translation services are encouraged to seek out the information book in the baggage claim area of the terminal. There they will find I-Speak language cards and a Limited English Proficiency phone, which offers a quick, convenient connection to quality interpreters who speak over 200 different languages.
  • If traveling internationally from the Chicago Midway International Airport (MDW), note that the airport’s on-site Seaway National Bank offers exchange services for converting your money into foreign currency. More than 200 currencies may be bought and sold at this location. For even faster service, you may call in your exchange ahead of your arrival.

Best time to book a flight from Midway

Have a flexible travel schedule? Discover the best time to fly from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Midway

Get recent, data-driven insights about flights from Midway including ideal travel times, pricing trends, and more.

When is the best time to book a flight from Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from Midway to Dallas/Fort Worth. Price data was last updated on November 14, 2025.

To ensure you get the cheapest price possible for a flight from Chicago Midway Airport, you should look to book at least 62 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago Midway Airport?

Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport (average of $58). Flying from Chicago Midway Airport in August will prove the most costly (average of $119). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

When is the cheapest time to fly from Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Midway to Dallas/Fort Worth. Price data was last updated on November 2, 2025.

Those who are seeking the cheapest fare on flights departing from Chicago Midway Airport would be wise to consider leaving during Tuesday evenings when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Saturday at noon when fares are usually the most expensive.

Which airlines fly from Chicago Midway Airport?

For flights departing from Chicago Midway Airport check dates and pricing for the following: Frontier, Southwest. These airlines depart to the following popular destinations: Dallas.

Southwest
Southwest
From $77
Frontier
Frontier
From $54
Delta
Delta
From $91
Volaris
Volaris
From $186

What are popular destinations to fly to from Chicago Midway Airport?

Some of the most frequent flights departing from Chicago Midway Airport everyday are: Atlanta (152 flights per day), Detroit (128 flights per day), and Minneapolis (87 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From $54
Orlando
Orlando
From $53
Dallas/Fort Worth
Dallas/Fort Worth
From $44
Washington, D.C.
Washington, D.C.
From $51

What is the cheapest place to fly to from Chicago Midway Airport?

The cheapest city to fly to from Chicago Midway Airport is Miami, with prices starting at $29. Explore other affordable destinations below.

Miami
Miami
From $29
New York
New York
From $29
Houston Hobby
Houston Hobby
From $29
Louisville Intl
Louisville Intl
From $38

Airline reviews for flights from Midway

Read reviews and ratings of airlines operating flights from Midway. Gain insights into the quality of service, in-flight amenities, customer experiences, and overall satisfaction to choose the best airline for your Midway travel. Please note that the reviews are sourced from user searches and were last updated on November 21, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches.
Read through reviews of airlines servicing Chicago Midway Airport, such as Southwest and Frontier. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,251 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,251 reviews
Southwest
8.0
Very good
4,251 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,102 reviews
Southwest
8.0
Very good
4,251 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Related info for your journey

Access useful and relevant information related to your journey from Midway. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated November 21, 2025.

  • What are the most popular destinations to fly to from Chicago Midway Airport?

    This month, the top selected destinations from Chicago Midway Airport are Atlanta, Orlando Airport, Dallas/Fort Worth Airport. Throughout the year, Atlanta, Las Vegas, Cancún are some of the top choices made by users flying from Chicago Midway Airport.

  • What is the cheapest flight from Chicago Midway Airport to anywhere?

    Users have flown out of Chicago Midway Airport for as low as $29 to Miami (prices may vary depending on the airline and departure time). On average, users have booked flights for $318 to fly from Chicago Midway Airport.

  • What are the cheapest airlines flying from Chicago Midway Airport to anywhere?

    Over the past few days, we've found that Allegiant Air, Frontier, and Spirit Airlines have the cheapest prices from Chicago Midway Airport. Allegiant Air flights from Chicago Midway Airport to Asheville Regional ($51), Frontier flights from Chicago Midway Airport to Aguascalients ($54), and Spirit Airlines flights from Chicago Midway Airport to Atlanta Hartsfield-Jackson ($63).

  • What is the cheapest premium economy flight from Chicago Midway Airport?

    Options for some of the cheapest premium economy flights from Chicago Midway Airport we have found on Cheapflights are as follows:
    Fly from Chicago Midway to Newark Airport starting at $54
    Fly from Chicago Midway to Philadelphia starting at $118
    Fly from Chicago Midway to Toronto Island Airport starting at $549
    Fly from Chicago Midway to Minneapolis starting at $700

  • What is the cheapest first class flight from Chicago Midway Airport?

    If you’re looking for a cheap first-class flight from Chicago Midway Airport, consider Philadelphia. Prices start at $280 so you can fly first-class even on a budget.

  • What is the cheapest month to fly from Chicago Midway Airport?

    March is currently the cheapest month to fly from Chicago Midway Airport. At this moment in time August is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

  • Where are the cheapest places to fly to from Chicago Midway Airport?

    Check out the cheapest flights from Chicago Midway Airport to embark to:
    Fly from Chicago to Dallas from $58 round trip
    Fly from Chicago to Atlanta from $58 round trip
    Fly from Chicago to Orlando from $58 round trip
    Fly from Chicago to Miami from $71 round trip
    Fly from Chicago to Houston from $79 round trip

  • Does the Chicago Midway International Airport (MDW) offer on-site accommodations?

    While the Chicago Midway International Airport (MDW) does not offer an on-site hotel at this time, there are ample accommodations available within a handful of miles to choose from, including The Courtyard by Marriot, which is only 9 minutes away.

  • What amenities are available at the Chicago Midway International Airport (MDW) for nursing mothers?

    The Chicago Midway International Airport (MDW) offers a Mother’s Room, which features a comfortable seating area, sink and wash area, and wall-mounted TV in a private setting. Additionally, lactation pods throughout the airport provide safe and private spaces for mothers to nurse or pump while traveling.

  • Does the Chicago Midway International Airport (MDW) offer quiet spaces for those looking to escape the excitement of a travel hub??

    Yes, in Concourse C of the Chicago Midway International Airport (MDW) you will find a Yoga Room, which offers passengers a place to retreat and meditate between the hours of 6 am and 10 pm.

  • Are there shopping opportunities available at the Chicago Midway International Airport (MDW)?

    Yes, the Chicago Midway International Airport (MDW) offers a wide variety of shopping options, from convenience stores and kiosks to popular companies like Build-A-Bear Workshop to smaller retailers offering unique, local souvenirs and gifts.

See more FAQs

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.