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Cheap flights to Midway from $59

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 6/8. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
BOS — MDW
Jun 2 — Jun 91
From?
To?
Sun 6/2
Sun 6/9
1 adult, Economy
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Flights to Midway in 2024

Find the latest flights to Midway in 2024, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 2,740,132 searches and data was last updated on May 28, 2024.

Popular in

June

Cheapest in

February

Average price

$285

Round-trip from

$70

One-way from

$59
High demand for flights, 14% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in May 2024
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From New York to Chicago
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One-way flight from New York to Chicago Midway (MDW)
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Cheap flights to Midway Airport in May & June 2024

Discover affordable flights and deals to Midway Airport in May and June 2024. In the last 7 days, Cheapflights users made a total of 2,740,132 searches and data was last updated on May 28, 2024.
These are some of the cheapest-priced fares users can find on flights departing to Chicago in May and June 2024. If these prices don't match your budget, be sure to check back soon for more deals.
Wed 6/56:00 amLGA - MDW
1 stop17h 58mFrontier
Wed 6/126:00 amMDW - LGA
1 stop13h 59mFrontier
Deal found 5/27$104
Tue 6/410:50 pmLGA - MDW
1 stop14h 10mFrontier
Tue 6/117:00 amMDW - LGA
1 stop12h 59mFrontier
Deal found 5/28$106
Tue 6/1110:52 amLGA - MDW
1 stop8h 55mFrontier
Wed 6/126:00 amMDW - LGA
1 stop13h 59mFrontier
Deal found 5/27$114
Wed 6/56:00 amLGA - MDW
1 stop17h 58mFrontier
Mon 6/1012:57 pmMDW - LGA
1 stop9h 18mFrontier
Deal found 5/28$115
Sat 6/810:50 pmLGA - MDW
1 stop13h 22mFrontier
Wed 6/126:00 amMDW - LGA
1 stop13h 59mFrontier
Deal found 5/28$116
Sat 6/810:50 pmLGA - MDW
1 stop13h 22mFrontier
Sat 6/157:00 amMDW - LGA
1 stop9h 08mFrontier
Deal found 5/28$119
Tue 6/116:00 amLGA - MDW
2 stops16h 20mFrontier
Wed 6/126:00 amMDW - LGA
1 stop13h 59mFrontier
Deal found 5/27$125
Wed 6/1210:59 pmLGA - MDW
1 stop13h 09mFrontier
Tue 6/187:00 amMDW - LGA
1 stop12h 59mFrontier
Deal found 5/27$133
Sat 6/810:50 pmLGA - MDW
1 stop13h 22mFrontier
Mon 7/15:55 amMDW - LGA
1 stop15h 05mFrontier
Deal found 5/28$138

Midway Airport 2024 flight deals

Explore flight deals for Midway Airport in 2024, offering the best prices and options to suit your preferences. In the last 7 days, Cheapflights users made a total of 2,740,132 searches and data were last updated on May 28, 2024.
These are some of the most attractive deals on flights to Chicago in 2024. Check back regularly for other flight deals.
Tue 6/1110:52 amLGA - MDW
1 stop8h 55mFrontier
Wed 6/126:00 amMDW - LGA
1 stop13h 59mFrontier
Deal found 5/27$114
Wed 6/56:00 amLGA - MDW
1 stop17h 58mFrontier
Mon 6/1012:57 pmMDW - LGA
1 stop9h 18mFrontier
Deal found 5/28$115
Sat 6/810:50 pmLGA - MDW
1 stop13h 22mFrontier
Wed 6/126:00 amMDW - LGA
1 stop13h 59mFrontier
Deal found 5/28$116
Sat 9/710:56 amLGA - MDW
1 stop10h 53mFrontier
Tue 9/109:44 pmMDW - LGA
1 stop11h 22mFrontier
Deal found 5/27$117
Sat 6/810:50 pmLGA - MDW
1 stop13h 22mFrontier
Sat 6/157:00 amMDW - LGA
1 stop9h 08mFrontier
Deal found 5/28$119
Tue 6/116:00 amLGA - MDW
2 stops16h 20mFrontier
Wed 6/126:00 amMDW - LGA
1 stop13h 59mFrontier
Deal found 5/27$125
Wed 9/410:56 amLGA - MDW
1 stop10h 53mFrontier
Mon 9/99:44 pmMDW - LGA
1 stop11h 22mFrontier
Deal found 5/27$127
Sat 8/244:20 pmLGA - MDW
1 stop6h 32mFrontier
Mon 8/266:05 amMDW - LGA
1 stop13h 54mFrontier
Deal found 5/27$129
Thu 9/510:56 amLGA - MDW
1 stop10h 53mFrontier
Sat 9/79:44 pmMDW - LGA
1 stop11h 22mFrontier
Deal found 5/28$130

Flights to Midway Airport departing soon

Discover available last-minute flight options to Midway Airport, providing immediate availability and potentially lower prices. In the last 7 days, Cheapflights users made a total of 2,740,132 searches and data was last updated on May 28, 2024.
Users traveling to Chicago last-minute should check out these flights departing soon. It's recommended that you verify the details of your last-minute flight before booking.
Wed 6/56:00 amLGA - MDW
1 stop17h 58mFrontier
Wed 6/126:00 amMDW - LGA
1 stop13h 59mFrontier
Deal found 5/27$104
Tue 6/410:50 pmLGA - MDW
1 stop14h 10mFrontier
Tue 6/117:00 amMDW - LGA
1 stop12h 59mFrontier
Deal found 5/28$106
Wed 6/56:00 amLGA - MDW
1 stop17h 58mFrontier
Mon 6/1012:57 pmMDW - LGA
1 stop9h 18mFrontier
Deal found 5/28$115
Wed 6/56:00 amLGA - MDW
1 stop17h 58mFrontier
Tue 6/116:00 amMDW - LGA
1 stop15h 00mFrontier
Deal found 5/28$142
Tue 6/410:50 pmLGA - MDW
1 stop14h 10mFrontier
Tue 6/117:00 amMDW - LGA
1 stop12h 59mFrontier
Deal found 5/26$143
Tue 6/410:50 pmLGA - MDW
1 stop14h 10mFrontier
Tue 6/187:00 amMDW - LGA
1 stop12h 59mFrontier
Deal found 5/27$147
Tue 6/410:50 pmLGA - MDW
1 stop14h 10mFrontier
Thu 6/66:56 amMDW - LGA
1 stop9h 12mFrontier
Deal found 5/28$151
Wed 6/56:00 amLGA - MDW
1 stop17h 58mFrontier
Sun 6/95:54 amMDW - LGA
1 stop14h 05mFrontier
Deal found 5/27$153
Mon 6/310:50 pmLGA - MDW
1 stop19h 22mFrontier
Wed 6/512:57 pmMDW - LGA
1 stop9h 46mFrontier
Deal found 5/27$155

One-way flights to Midway Airport

Explore one-way flight options to Midway Airport for greater flexibility in your travel plans. Find up-to-date pricing and availability for one-way flights. In the last 7 days, Cheapflights users made a total of 2,740,132 searches and data was last updated on May 28, 2024.
Choose from one of these one-way flights departing to Chicago. Reserve a round-trip flight to Chicago instead by utilizing the search form above.
Sat 6/810:50 pmLGA - MDW
1 stop13h 22mFrontier
Deal found 5/28$59
Wed 6/56:00 amLGA - MDW
1 stop17h 58mFrontier
Deal found 5/28$60
Sat 6/810:50 pmLGA - MDW
1 stop13h 22mFrontier
Deal found 5/26$61
Wed 6/126:00 amLGA - MDW
1 stop17h 58mFrontier
Deal found 5/27$63
Wed 6/510:59 pmLGA - MDW
1 stop23h 46mFrontier
Deal found 5/26$64
Tue 6/116:00 amLGA - MDW
2 stops16h 20mFrontier
Deal found 5/27$65
Sat 6/810:50 pmLGA - MDW
1 stop13h 22mFrontier
Deal found 5/27$67
Tue 6/116:00 amLGA - MDW
2 stops16h 20mFrontier
Deal found 5/27$69
Tue 6/119:50 amLGA - MDW
1 stop13h 37mMultiple Airlines
Deal found 5/27$71

Direct flights to Midway Airport

Tue 6/259:05 amLGA - MDW
Nonstop2h 25mSouthwest
Tue 6/253:45 pmMDW - LGA
Nonstop2h 10mSouthwest
Deal found 5/28$228
Mon 6/176:35 amLGA - MDW
Nonstop2h 20mSouthwest
Tue 6/187:55 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 5/28$236
Sat 6/156:30 amLGA - MDW
Nonstop2h 20mSouthwest
Mon 6/173:45 pmMDW - LGA
Nonstop2h 10mSouthwest
Deal found 5/27$237
Tue 7/232:10 pmLGA - MDW
Nonstop2h 25mSouthwest
Wed 7/317:25 amMDW - LGA
Nonstop2h 05mSouthwest
Deal found 5/27$253
Mon 7/19:05 amLGA - MDW
Nonstop2h 25mSouthwest
Tue 7/27:25 amMDW - LGA
Nonstop2h 05mSouthwest
Deal found 5/27$264
Mon 6/109:10 amLGA - MDW
Nonstop2h 25mSouthwest
Thu 6/135:50 pmMDW - LGA
Nonstop2h 10mSouthwest
Deal found 5/28$349

Find flights to Midway within your budget

Locate flights to Midway that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 2,740,132 searches and data was last updated on May 28, 2024.

Fly from

Any airport

Budget

$114 - $264

Route

Depart

Return

Price

New York LaGuardiaChicago Midway

LGA - MDW

LGAMDW

New York LaGuardia

Tue 6/11

1 stop8h 55m

Chicago Midway

Wed 6/12

1 stop13h 59m

$114

New York LaGuardiaChicago Midway

LGA - MDW

LGAMDW

New York LaGuardia

Sat 6/8

1 stop13h 22m

Chicago Midway

Wed 6/12

1 stop13h 59m

$116

New York LaGuardiaChicago Midway

LGA - MDW

LGAMDW

New York LaGuardia

Sat 6/8

1 stop13h 22m

Chicago Midway

Sat 6/15

1 stop9h 08m

$119

New York LaGuardiaChicago Midway

LGA - MDW

LGAMDW

New York LaGuardia

Tue 6/11

2 stops16h 20m

Chicago Midway

Wed 6/12

1 stop13h 59m

$125

New York LaGuardiaChicago Midway

LGA - MDW

LGAMDW

New York LaGuardia

Sat 8/24

1 stop6h 32m

Chicago Midway

Mon 8/26

1 stop13h 54m

$129

NewarkChicago Midway

EWR - MDW

EWRMDW

Newark

Tue 7/9

1 stop5h 04m

Chicago Midway

Wed 7/10

1 stop5h 56m

$203

NewarkChicago Midway

EWR - MDW

EWRMDW

Newark

Wed 6/19

1 stop13h 40m

Chicago Midway

Mon 6/24

1 stop11h 57m

$236

NewarkChicago Midway

EWR - MDW

EWRMDW

Newark

Fri 6/21

1 stop10h 23m

Chicago Midway

Mon 6/24

1 stop11h 57m

$258

New York LaGuardiaChicago Midway

LGA - MDW

LGAMDW

New York LaGuardia

Tue 6/25

2 stops11h 55m

Chicago Midway

Tue 6/25

2 stops12h 25m

$264

Flights are sorted by cheapest first

Deals found on 5/27

Best time to book a flight to Midway

Have a flexible travel schedule? Discover the best time to fly to 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.

Temperature and rainfall in Midway by month

Plan your trip to Midway by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

23 - 73.4 °F

If weather is an important factor for your trip to Midway, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

When is the best time to book a flight to Midway?

Use this chart to determine the optimal time to book a round-trip flight to Midway. Price data was last updated on May 24, 2024.
Booking 77 days in advance of your planned departure date is, on average, the best time to get cheap flights to Midway. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
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When is the cheapest time to fly to Midway?

Use this chart to determine the cheapest time to fly round-trip to Midway. Price data was last updated on May 26, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Users looking for the lowest fares to Midway should consider flying on Saturday mornings, when prices are typically cheapest. Budget-minded travelers will want to avoid Sunday mornings, when prices are usually at their highest.
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Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated May 28, 2024.
To help decide which airline to fly to Chicago, see what other customers have to say about Frontier, Southwest and Allegiant Air. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
5,984 reviews
Check prices

Overall

8.2

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.3

Entertainment

7.8

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Southwest
8.2
Very good
5,984 reviews
Southwest
8.2
Very good
5,984 reviews
Check prices

Overall

8.2

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.3

Entertainment

7.8

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Delta
8.0
Very good
10,476 reviews
Southwest
8.2
Very good
5,984 reviews
Check prices

Overall

8.2

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.3

Entertainment

7.8

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

WestJet
7.5
Good
2,871 reviews
Southwest
8.2
Very good
5,984 reviews
Check prices

Overall

8.2

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.3

Entertainment

7.8

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Allegiant Air
7.5
Good
1,003 reviews
Southwest
8.2
Very good
5,984 reviews
Check prices

Overall

8.2

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.3

Entertainment

7.8

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Porter Airlines
7.4
Good
395 reviews
Southwest
8.2
Very good
5,984 reviews
Check prices

Overall

8.2

Comfort

8.1

Crew

8.7

Boarding

8.3

Food

7.3

Entertainment

7.8

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Chicago Midway International Airport (MDW) is developing into an important hub for domestic air travel in the United States. In 2010, more than 17 million passengers passed through its gates, gaining connections to hundreds of American and international destinations.

Flights to Chicago Midway International Airport are mainly provided by Dallas-based low-cost carrier Southwest Airlines, offering cheap flights to a host of American and Canadian destinations. Most other airlines fly into Chicago’s other major airport, O’Hare.

There’s quite a lot to see and do in Chicago Midway, including a lovely central area known as Midway Boulevard. Full of shops, restaurants and cafes, Midway Boulevard is the perfect place to pull up a chair and people-watch.

  • Can I find cheaper flights to Midway if I am willing to have layovers?

    Yes, flights with layovers are often cheaper than direct flights. Keep an eye out for flight deals to Midway on Cheapflights that require 1 or 2 stops for potential cost savings.

  • What is the best airline to fly to Midway?

    Based on reviews from Cheapflights users, Frontier is rated the highest out of the airlines that fly to Midway.

  • What is the cheapest airport to fly to in Midway?

    Chicago Midway Airport is currently the cheapest airport to fly to in Midway. One-way flights to Chicago Midway Airport typically cost $26, while round-trip flights cost around $43.

  • How much is a round-trip flight to Midway?

    A round-trip flight to Midway will typically cost around $147, however they can be found for as little as $43.

  • Where does the fastest flight to Midway depart from?

    For those looking to save time traveling to Midway, St. Louis offers the quickest one-way flight (1 hour 5 minutes).

  • Does Chicago Midway Airport have rental cars?

    Yes. Those touching down at Chicago Midway Airport can take advantage of the rental car services offered upon their arrival.

  • Are there hotels close to Chicago Midway Airport?

    Yes. Chicago Midway Airport has hotels nearby for those requiring accommodations. Midway Airport 2 Bedroom with full Kitchen is the closest property to Chicago Midway Airport (0.0 mi away from Chicago Midway Airport).

See more FAQs

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Other Chicago travelers fly to these airports near Midway.

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Search flights to Midway by cabin class

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