$44+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — CUN
Jan 22 — Jan 291
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 23, 2025.
Cheapest airline | Emirates |
|---|---|
Good round-trip deal | $66 or less |
Good one-way deal | $58 or less |
Find flights from Midway
Cheapest flights from MidwayExplore the most affordable flight options available from Midway. Find the lowest fares based on data from user searches, with prices last updated on December 23, 2025.
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 23, 2025.
This CheapOair deal was found by Cheapflights users on 12/20. 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 1/239:45 amMDW - DFW
Nonstop2h 45mFrontier
Fri 1/301:30 pmDFW - MDW
Nonstop2h 19mFrontier
Deal found 12/20![Frontier logo]()
$89
This Super.com deal was found by Cheapflights users on 12/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/119:15 amMDW - DFW
Nonstop2h 50mFrontier
Sun 1/183:00 pmDFW - MDW
Nonstop2h 20mFrontier
Deal found 12/21![Frontier logo]()
$92
This Expedia deal was found by Cheapflights users on 12/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/219:15 amMDW - DFW
Nonstop2h 45mFrontier
Sat 2/2810:44 amDFW - MDW
1 stop10h 55mFrontier
Deal found 12/22![Frontier logo]()
$93
This Frontier deal was found by Cheapflights users on 12/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/124:31 pmMDW - MCO
Nonstop2h 47mFrontier
Tue 1/276:10 amMCO - MDW
1 stop6h 55mFrontier
Deal found 12/21![Frontier logo]()
$93
This CheapOair deal was found by Cheapflights users on 12/21. 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.
Sat 2/149:15 amMDW - DFW
Nonstop2h 45mFrontier
Sat 2/2110:44 amDFW - MDW
1 stop10h 49mFrontier
Deal found 12/21![Frontier logo]()
$94
This Expedia deal was found by Cheapflights users on 12/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/1910:07 amMDW - MCO
Nonstop2h 46mFrontier
Mon 1/265:55 pmMCO - MDW
Nonstop3h 03mFrontier
Deal found 12/22![Frontier logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 12/22. 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.
Wed 3/1111:55 amMDW - DFW
Nonstop2h 43mFrontier
Wed 3/188:30 amDFW - MDW
Nonstop2h 25mFrontier
Deal found 12/22![Frontier logo]()
$97
This Frontier deal was found by Cheapflights users on 12/23. 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 2/11:00 pmMDW - MCO
Nonstop2h 49mFrontier
Wed 2/46:10 amMCO - MDW
1 stop6h 55mFrontier
Deal found 12/23![Frontier logo]()
$97
This Frontier deal was found by Cheapflights users on 12/22. 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.
Fri 2/137:45 amMDW - DFW
Nonstop2h 52mFrontier
Sat 2/141:00 pmDFW - MDW
Nonstop2h 19mFrontier
Deal found 12/22![Frontier logo]()
$98
This Expedia deal was found by Cheapflights users on 12/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/219:15 amMDW - MCO
1 stop10h 32mFrontier
Thu 2/2612:20 pmMCO - MDW
Nonstop3h 06mFrontier
Deal found 12/22![Frontier logo]()
$98
This Priceline deal was found by Cheapflights users on 12/21. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/56:15 amMDW - MIA
Nonstop3h 17mFrontier
Wed 1/711:43 amMIA - MDW
Nonstop3h 23mFrontier
Deal found 12/21![Frontier logo]()
$99
This Frontier deal was found by Cheapflights users on 12/22. 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.
Wed 1/211:20 pmMDW - MCO
1 stop9h 41mFrontier
Thu 2/1912:20 pmMCO - MDW
Nonstop3h 06mFrontier
Deal found 12/22![Frontier logo]()
$99
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 23, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches
Fly to
Cancún
Route
Depart
Return
Price
ChicagoDallas
MDW - DFW
MDWDFW
Chicago Midway
Fri 2/13
7:45 am-10:37 am
Nonstop2h 52m
Dallas/Fort Worth
Sat 2/14
1:00 pm-3:19 pm
Nonstop2h 19m
$98
ChicagoDallas
MDW - DFW
MDWDFW
Chicago Midway
Sat 2/14
9:15 am-12:00 pm
Nonstop2h 45m
Dallas/Fort Worth
Mon 2/16
12:05 pm-2:29 pm
Nonstop2h 24m
$104
ChicagoDallas
MDW - DFW
MDWDFW
Chicago Midway
Thu 2/12
3:00 pm-5:46 pm
Nonstop2h 46m
Dallas/Fort Worth
Mon 2/16
12:05 pm-2:29 pm
Nonstop2h 24m
$107
ChicagoDallas
MDW - DFW
MDWDFW
Chicago Midway
Fri 1/9
9:15 am-12:05 pm
Nonstop2h 50m
Dallas/Fort Worth
Mon 1/12
1:15 pm-3:33 pm
Nonstop2h 18m
$116
ChicagoOrlando
MDW - MCO
MDWMCO
Chicago Midway
Sun 1/18
6:30 pm-7:53 am
1 stop12h 23m
Orlando
Wed 1/21
6:10 am-12:05 pm
1 stop6h 55m
$136
ChicagoDallas
MDW - DFW
MDWDFW
Chicago Midway
Sat 2/14
9:15 am-12:00 pm
Nonstop2h 45m
Dallas/Fort Worth
Sun 2/15
9:20 am-7:59 pm
1 stop10h 39m
$138
ChicagoFort Lauderdale
MDW - FLL
MDWFLL
Chicago Midway
Tue 1/27
8:30 am-12:40 pm
Nonstop3h 10m
Fort Lauderdale
Sat 1/31
6:40 am-8:50 am
Nonstop3h 10m
$157
ChicagoDallas
MDW - DFW
MDWDFW
Chicago Midway
Fri 2/20
7:45 am-10:37 am
Nonstop2h 52m
Dallas/Fort Worth
Sun 2/22
9:20 am-7:59 pm
1 stop10h 39m
$161
ChicagoNewark
MDW - EWR
MDWEWR
Chicago Midway
Mon 1/5
8:15 am-9:35 pm
1 stop12h 20m
Newark
Mon 1/26
6:00 am-11:45 am
1 stop6h 45m
$162
ChicagoNew York
MDW - JFK
MDWJFK
Chicago Midway
Thu 1/22
5:01 pm-1:03 am
1 stop7h 02m
New York John F Kennedy Intl
Thu 1/29
6:10 am-11:45 am
1 stop6h 35m
$162
Showing 1-10 of 60 results
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
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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 23, 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 December 19, 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 $254). 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.
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 (155 flights per day), Orlando (150 flights per day), and Detroit (136 flights per day).
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.
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 23, 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.
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Food
7.0
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN