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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 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Jan 2 — Jan 91
Fri 1/2
Fri 1/9
1 adult, Economy
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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 December 3, 2025.

Cheapest airline

Emirates

Good round-trip deal

$66 or less

Good one-way deal

$65 or less
On average, Emirates currently has the cheapest one-way flight from Chicago Midway (avg. price of $1,161).
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Price to beat on a round-trip flight from Chicago Midway.
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Price to beat on a one-way flight from Chicago Midway.
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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 December 3, 2025.

This FlightHub deal was found by Cheapflights users on 12/1. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/1811:05 amMDW - DFW
Nonstop2h 43mFrontier
Sun 1/183:00 pmDFW - MDW
Nonstop2h 20mFrontier
Deal found 12/1$89
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Thu 1/1511:05 amMDW - DFW
Nonstop2h 43mFrontier
Sun 1/183:00 pmDFW - MDW
Nonstop2h 20mFrontier
Deal found 12/2$90
This Frontier deal was found by Cheapflights users on 12/2. 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.
Thu 1/1511:05 amMDW - DFW
Nonstop2h 43mFrontier
Thu 1/226:10 amDFW - MDW
1 stop5h 35mFrontier
Deal found 12/2$93
This Frontier deal was found by Cheapflights users on 12/2. 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.
Sun 12/218:00 amMDW - DFW
Nonstop2h 42mFrontier
Fri 1/91:15 pmDFW - MDW
Nonstop2h 18mFrontier
Deal found 12/2$94
This CheapOair deal was found by Cheapflights users on 12/2. 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.
Mon 1/1910:07 amMDW - MCO
Nonstop2h 46mFrontier
Sun 1/253:15 pmMCO - MDW
1 stop8h 04mFrontier
Deal found 12/2$94
This CheapOair deal was found by Cheapflights users on 12/2. 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 1/28:00 amMDW - DFW
Nonstop2h 42mFrontier
Fri 1/91:15 pmDFW - MDW
Nonstop2h 18mFrontier
Deal found 12/2$95
This Kiwi.com deal was found by Cheapflights users on 12/3. 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.
Mon 1/129:15 amMDW - MCO
1 stop12h 42mFrontier
Thu 1/158:30 amMCO - MDW
Nonstop3h 02mFrontier
Deal found 12/3$95
This CheapOair deal was found by Cheapflights users on 12/2. 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.
Mon 1/129:15 amMDW - DFW
Nonstop2h 50mFrontier
Mon 1/191:00 pmDFW - MDW
Nonstop2h 19mFrontier
Deal found 12/2$96
This Kiwi.com deal was found by Cheapflights users on 12/2. 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 1/168:28 amMDW - MCO
1 stop22h 03mMultiple Airlines
Fri 1/235:49 pmMCO - MDW
Nonstop3h 03mMultiple Airlines
Deal found 12/2$96
This Kiwi.com deal was found by Cheapflights users on 11/30. 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 12/162:49 pmMDW - DFW
1 stop8h 05mFrontier
Mon 1/191:00 pmDFW - MDW
Nonstop2h 19mFrontier
Deal found 11/30$97
This Southwest deal was found by Cheapflights users on 12/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/211:55 pmMDW - MCO
1 stop5h 05mSouthwest
Tue 1/279:25 amMCO - MDW
Nonstop2h 50mSouthwest
Deal found 12/1$97
This Trip.com deal was found by Cheapflights users on 12/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/309:45 amMDW - DFW
Nonstop2h 45mFrontier
Mon 2/26:10 amDFW - MDW
1 stop5h 35mFrontier
Deal found 12/3$98

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 December 3, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Cancún

Route

Depart

Return

Price

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 1/13

1:55 pm-8:00 pm

1 stop5h 05m

Orlando

Tue 1/20

10:45 am-2:30 pm

1 stop4h 45m

$98

ChicagoPhoenix

MDW - PHX

MDWPHX

Chicago Midway

Sat 2/21

7:15 pm-10:15 pm

Nonstop4h 00m

Phoenix Sky Harbor Intl

Wed 2/25

5:00 am-9:15 am

Nonstop3h 15m

$133

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 1/8

6:05 am-9:10 am

Nonstop2h 05m

New York LaGuardia

Thu 1/8

9:45 pm-11:15 pm

Nonstop2h 30m

$134

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sun 2/15

6:05 pm-9:10 pm

Nonstop2h 05m

New York LaGuardia

Thu 2/19

11:45 am-1:20 pm

Nonstop2h 35m

$135

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sun 1/11

6:05 am-9:10 am

Nonstop2h 05m

New York LaGuardia

Sat 1/17

8:00 am-9:30 am

Nonstop2h 30m

$136

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 1/16

8:10 pm-11:10 pm

Nonstop2h 00m

New York LaGuardia

Tue 1/20

9:15 am-10:55 am

Nonstop2h 40m

$138

ChicagoPhoenix

MDW - PHX

MDWPHX

Chicago Midway

Sat 2/7

2:55 pm-5:50 pm

Nonstop3h 55m

Phoenix Sky Harbor Intl

Sat 2/14

4:10 pm-8:20 pm

Nonstop3h 10m

$147

ChicagoPhoenix

MDW - PHX

MDWPHX

Chicago Midway

Tue 1/13

8:15 am-1:35 pm

1 stop6h 20m

Phoenix Sky Harbor Intl

Sat 1/17

4:55 pm-9:10 pm

Nonstop3h 15m

$149

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 12/31

5:15 pm-8:00 pm

Nonstop2h 45m

Houston Hobby

Thu 1/8

8:30 pm-10:55 pm

Nonstop2h 25m

$149

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 1/27

3:15 pm-10:00 pm

1 stop5h 45m

Miami

Wed 2/4

2:35 pm-4:50 pm

Nonstop3h 15m

$150

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/2

Showing 1-10 of 60 results
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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 December
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars

*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, Mytrip has been found to have the most accurate pricing. Users can find the same prices on deals on Cheapflights as Mytrip 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 Mytrip the highest out of those offering flight deals from Chicago Midway Airport. Mytrip 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 December 3, 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 Cancún. Price data was last updated on November 28, 2025.

To ensure you get the cheapest price possible for a flight from Chicago Midway Airport, you should look to book at least 57 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, April is the cheapest month in which you can book a flight from Chicago Midway Airport (average of $255). Flying from Chicago Midway Airport in January will prove the most costly (average of $430). 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: Southwest, Delta, Volaris, Aeromexico, LATAM Airlines. These airlines depart to the following popular destinations: Cancún.

Southwest
Southwest
From $77
Frontier
Frontier
From $39
Delta
Delta
From $91
Volaris
Volaris
From $185

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 (158 flights per day), Atlanta (148 flights per day), and Minneapolis (99 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From $37
Orlando
Orlando
From $37
Dallas/Fort Worth
Dallas/Fort Worth
From $42
New York
New York
From $33

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 $28. Explore other affordable destinations below.

Miami
Miami
From $28
New York
New York
From $33
Orlando
Orlando
From $37
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From $37

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 December 3, 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, Delta, and LATAM Airlines. 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
4,254 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,254 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Delta
7.9
Good
8,009 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
LATAM Airlines
7.5
Good
1,890 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Aeromexico
7.5
Good
1,653 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Volaris
6.7
Okay
1,156 reviews
Southwest
8.0
Very good
4,254 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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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 December 3, 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, Miami. 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 $28 to Miami (prices may vary depending on the airline and departure time). On average, users have booked flights for $358 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 Spirit Airlines have the cheapest prices from Chicago Midway Airport. Frontier flights from Chicago Midway Airport to Aguascalients ($39), Allegiant Air flights from Chicago Midway Airport to Asheville Regional ($51), 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?

    April is currently the cheapest month to fly from Chicago Midway Airport. At this moment in time January 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 Miami from $49 round trip
    Fly from Chicago to Atlanta from $50 round trip
    Fly from Chicago to Orlando from $54 round trip
    Fly from Chicago to Dallas from $58 round trip
    Fly from Chicago to New York from $65 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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