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Midway

$50+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — LAS
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Cheapest airline

Emirates

Good round-trip deal

$61 or less

Good one-way deal

$49 or less
On average, Emirates currently has the cheapest one-way flight from Chicago Midway (avg. price of $1,146).
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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 September 11, 2025.

Tue 9/232:32 pmMDW - ATL
Nonstop2h 01mFrontier
Fri 10/310:46 pmATL - MDW
Nonstop1h 55mFrontier
Deal found 9/8$78
Sat 10/186:15 amMDW - ATL
Nonstop2h 14mFrontier
Fri 10/2410:46 pmATL - MDW
Nonstop2h 00mFrontier
Deal found 9/9$80
Wed 9/249:00 amMDW - ATL
Nonstop1h 58mFrontier
Sat 10/189:44 pmATL - MDW
Nonstop2h 03mFrontier
Deal found 9/10$82
Sat 10/186:15 amMDW - ATL
Nonstop2h 14mFrontier
Tue 11/410:38 amATL - MDW
Nonstop2h 00mFrontier
Deal found 9/9$84
Sat 10/46:15 amMDW - ATL
Nonstop2h 07mFrontier
Mon 10/610:46 pmATL - MDW
Nonstop1h 55mFrontier
Deal found 9/9$85
Wed 9/249:00 amMDW - ATL
Nonstop1h 58mFrontier
Tue 9/303:00 pmATL - MDW
Nonstop1h 58mFrontier
Deal found 9/9$87
Sat 9/276:15 amMDW - ATL
Nonstop2h 07mFrontier
Fri 10/310:46 pmATL - MDW
Nonstop1h 55mFrontier
Deal found 9/10$88
Wed 9/249:00 amMDW - ATL
Nonstop1h 58mFrontier
Wed 10/13:00 pmATL - MDW
Nonstop1h 58mFrontier
Deal found 9/10$89
Wed 9/249:00 amMDW - ATL
Nonstop1h 58mFrontier
Fri 10/310:46 pmATL - MDW
Nonstop1h 55mFrontier
Deal found 9/10$90
Mon 9/296:20 amMDW - ATL
Nonstop2h 07mFrontier
Tue 9/303:00 pmATL - MDW
Nonstop1h 58mFrontier
Deal found 9/9$91
Thu 10/99:26 pmMDW - ATL
Nonstop2h 05mFrontier
Tue 10/1412:40 pmATL - MDW
Nonstop1h 58mFrontier
Deal found 9/10$92
Thu 10/210:13 amMDW - DFW
Nonstop2h 38mFrontier
Mon 10/610:41 amDFW - MDW
Nonstop2h 30mFrontier
Deal found 9/9$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 September 11, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Las Vegas

Route

Depart

Return

Price

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Thu 10/23

5:20 pm-8:01 pm

Nonstop2h 41m

Dallas/Fort Worth

Sun 10/26

9:01 pm-11:20 pm

Nonstop2h 19m

$102

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Sat 10/11

5:20 pm-8:01 pm

Nonstop2h 41m

Dallas/Fort Worth

Mon 10/13

9:57 pm-12:16 am

Nonstop2h 19m

$105

ChicagoDallas

MDW - DFW

MDWDFW

Chicago Midway

Wed 11/12

2:06 pm-8:51 pm

1 stop6h 45m

Dallas/Fort Worth

Mon 11/17

3:39 pm-5:59 pm

Nonstop2h 20m

$109

ChicagoAtlanta

MDW - ATL

MDWATL

Chicago Midway

Sat 1/17

12:45 pm-3:35 pm

Nonstop1h 50m

Atlanta Hartsfield-Jackson

Sat 1/17

5:45 pm-6:40 pm

Nonstop1h 55m

$117

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 11/5

8:25 am-11:30 am

Nonstop2h 05m

New York LaGuardia

Sat 11/8

2:15 pm-3:45 pm

Nonstop2h 30m

$128

ChicagoHouston

MDW - HOU

MDWHOU

Chicago Midway

Wed 10/8

5:15 am-7:50 am

Nonstop2h 35m

Houston Hobby

Wed 10/15

9:15 pm-11:35 pm

Nonstop2h 20m

$133

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Tue 10/28

8:05 pm-11:35 pm

Nonstop2h 30m

Orlando

Tue 11/4

4:35 pm-6:25 pm

Nonstop2h 50m

$133

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 12/9

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Thu 12/11

6:00 am-7:30 am

Nonstop2h 30m

$138

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 11/18

11:15 am-5:05 pm

1 stop4h 50m

New York LaGuardia

Wed 11/19

6:15 am-11:25 am

1 stop6h 10m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 11/5

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Sun 11/9

7:15 am-8:45 am

Nonstop2h 30m

$139

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 60 results
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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 September 11, 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 Las Vegas. Price data was last updated on August 29, 2025.

To ensure you get the cheapest price possible for a flight from Chicago Midway Airport, you should look to book at least 71 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, November is the cheapest month in which you can book a flight from Chicago Midway Airport (average of $92). Flying from Chicago Midway Airport in July will prove the most costly (average of $204). 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 Las Vegas. Price data was last updated on September 7, 2025.

Those who are seeking the cheapest fare on flights departing from Chicago Midway Airport would be wise to consider leaving during Wednesday evenings when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Sunday 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: Southwest, Frontier, Spirit Airlines, United Airlines, Delta. These airlines depart to the following popular destinations: Las Vegas.

Southwest
Southwest
From $77
Frontier
Frontier
From $39
Delta
Delta
From $88
Volaris
Volaris
From $217

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 (232 flights per day), Atlanta (125 flights per day), and Minneapolis (89 flights per day).

Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From $60
Washington, D.C.
Washington, D.C.
From $54
Orlando
Orlando
From $43
Dallas/Fort Worth
Dallas/Fort Worth
From $44

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

The cheapest city to fly to from Chicago Midway Airport is Pittsburgh, with prices starting at $33. Explore other affordable destinations below.

Pittsburgh
Pittsburgh
From $33
Grand Rapids Gerald R. Ford Intl
Grand Rapids Gerald R. Ford Intl
From $38
Minneapolis St Paul
Minneapolis St Paul
From $38
Orlando
Orlando
From $43

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 September 11, 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 United 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
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Food

7.0

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

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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 September 11, 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 Las Vegas, Atlanta, Orlando 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 $33 to Pittsburgh (prices may vary depending on the airline and departure time). On average, users have booked flights for $280 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 Philadelphia starting at $118
    Fly from Chicago Midway to Toronto Island Airport starting at $877
    Fly from Chicago Midway to Minneapolis starting at $1,172
    Fly from Chicago Midway to Atlanta starting at $1,233

  • 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?

    November is currently the cheapest month to fly from Chicago Midway Airport. At this moment in time July 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 Atlanta from $51 round trip
    Fly from Chicago to Philadelphia from $52 round trip
    Fly from Chicago to Houston from $56 round trip
    Fly from Chicago to Dallas from $58 round trip
    Fly from Chicago to Baltimore from $74 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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