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Midway

$53+ 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — DFW
Jul 20 — Jul 271
Mon 7/20
Mon 7/27
1 adult, Economy
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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 June 20, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 7/14

5:15 am-8:15 am

Nonstop2h 00m

New York LaGuardia

Tue 7/21

9:30 pm-11:00 pm

Nonstop2h 30m

$187

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 8/8

3:10 pm-6:15 pm

Nonstop2h 05m

New York LaGuardia

Mon 8/10

8:55 pm-10:15 pm

Nonstop2h 20m

$200

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Wed 8/12

1:00 pm-8:10 pm

2 stops6h 10m

Miami

Wed 8/19

11:50 am-8:10 pm

2 stops9h 20m

$201

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 7/7

5:15 am-8:15 am

Nonstop2h 00m

New York LaGuardia

Wed 7/8

10:55 am-12:15 pm

Nonstop2h 20m

$202

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 7/23

5:15 am-8:15 am

Nonstop2h 00m

New York LaGuardia

Fri 7/24

6:00 am-7:20 am

Nonstop2h 20m

$207

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 7/31

7:45 pm-11:00 pm

Nonstop2h 15m

New York LaGuardia

Thu 8/6

6:00 am-7:15 am

Nonstop2h 15m

$207

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 8/1

5:00 am-8:00 am

Nonstop2h 00m

New York LaGuardia

Mon 8/10

6:00 am-7:15 am

Nonstop2h 15m

$217

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 7/30

5:15 pm-8:20 pm

Nonstop2h 05m

New York LaGuardia

Mon 8/10

8:55 pm-10:15 pm

Nonstop2h 20m

$220

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 8/6

3:20 pm-11:20 pm

1 stop7h 00m

New York LaGuardia

Wed 8/12

9:35 pm-10:50 pm

Nonstop2h 15m

$222

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 9/15

6:05 am-12:18 pm

1 stop5h 13m

Newark

Tue 9/29

6:00 am-9:07 am

1 stop4h 07m

$223

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/19

Showing 1-10 of 60 resultsSorted by cheapest first
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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 June
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
eDreamsPrice Accuracy2 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star
Super.comPrice Accuracy-Trust Score*3 stars
CheapflightsfaresPrice Accuracy2 starsTrust 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, FlightHub has been found to have the most accurate pricing. Users can find the same prices on deals on Cheapflights as FlightHub 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 FlightHub the highest out of those offering flight deals from Chicago Midway Airport. FlightHub 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 June 20, 2026.
  • 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.

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

Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport (average of $166). Flying from Chicago Midway Airport in June will prove the most costly (average of $350). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

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 $56
Volaris
Volaris
From $226
Delta
Delta
From $88

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

Some of the most frequent flights departing from Chicago Midway Airport everyday are: Detroit (202 flights per day), Atlanta (179 flights per day), and Orlando (122 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From $60
Dallas/Fort Worth
Dallas/Fort Worth
From $74
New York
New York
From $93
Washington, D.C.
Washington, D.C.
From $98

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

The cheapest city to fly to from Chicago Midway Airport is Valparaiso Destin-Ft Walton Beach, with prices starting at $49. Explore other affordable destinations below.

Valparaiso Destin-Ft Walton Beach
Valparaiso Destin-Ft Walton Beach
From $49
Asheville Regional
Asheville Regional
From $52
Knoxville McGhee Tyson
Knoxville McGhee Tyson
From $54
Pittsburgh
Pittsburgh
From $58

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

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.

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 June 13, 2026.

Those who are seeking the cheapest fare on flights departing from Chicago Midway Airport would be wise to consider leaving during Tuesday at noon 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.

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 June 20, 2026. 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
7.9
Good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Entertainment

7.5

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
7.9
Good
4,242 reviews
Southwest
7.9
Good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Entertainment

7.5

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
5.6
Fair
2,877 reviews
Southwest
7.9
Good
4,242 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Entertainment

7.5

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

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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 June 20, 2026.

  • 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, Las Vegas, Orlando Airport. Throughout the year, Atlanta, Las Vegas, Orlando Airport 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 $49 to Valparaiso, Florida (prices may vary depending on the airline and departure time). On average, users have booked flights for $340 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 Frontier, Allegiant Air, and Porter Airlines have the cheapest prices from Chicago Midway Airport. Frontier flights from Chicago Midway Airport to Atlanta Hartsfield-Jackson ($56), Allegiant Air flights from Chicago Midway Airport to Asheville Regional ($58), and Porter Airlines flights from Chicago Midway Airport to Montreal ($69).

  • 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 Orlando Airport starting at $187
    Fly from Chicago Midway to Dallas/Fort Worth Airport starting at $386

  • 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 Minneapolis. Prices start at $546 so you can fly first-class even on a budget.

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

    October is currently the cheapest month to fly from Chicago Midway Airport. At this moment in time June 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 Valparaiso from $92 round trip
    Fly from Chicago to Knoxville from $100 round trip
    Fly from Chicago to Minneapolis from $109 round trip
    Fly from Chicago to Asheville from $109 round trip
    Fly from Chicago to Cleveland from $117 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.

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