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Cheap flights to Midway from $58

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 8/20. 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 4 — Jun 111
From?
To?
Tue 6/4
Tue 6/11
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 2,784,634 searches and data was last updated on May 30, 2024.

Popular in

June

Cheapest in

February

Average price

$285

Round-trip from

$50

One-way from

$58
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 2,784,634 searches and data was last updated on May 30, 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 6/510:59 pmLGA - MDW
1 stop13h 09mFrontier
Wed 6/1212:57 pmMDW - LGA
1 stop9h 46mFrontier
Deal found 5/29$115
Sat 6/810:50 pmLGA - MDW
1 stop13h 22mFrontier
Mon 6/1012:57 pmMDW - LGA
1 stop9h 18mFrontier
Deal found 5/29$126
Wed 6/510:59 pmLGA - MDW
1 stop23h 46mFrontier
Tue 6/117:00 amMDW - LGA
1 stop12h 59mFrontier
Deal found 5/29$130
Tue 6/116:00 amLGA - MDW
2 stops16h 20mFrontier
Wed 6/126:00 amMDW - LGA
1 stop13h 59mFrontier
Deal found 5/29$135
Wed 6/126:00 amLGA - MDW
1 stop17h 58mFrontier
Tue 6/187:00 amMDW - LGA
1 stop12h 59mFrontier
Deal found 5/30$139
Sat 6/810:50 pmLGA - MDW
1 stop13h 22mFrontier
Mon 7/15:55 amMDW - LGA
1 stop15h 05mFrontier
Deal found 5/28$143
Tue 6/1110:50 pmLGA - MDW
1 stop14h 10mFrontier
Tue 6/187:00 amMDW - LGA
1 stop12h 59mFrontier
Deal found 5/29$148
Wed 6/199:45 pmLGA - MDW
Nonstop2h 25mSouthwest
Fri 6/217:55 amMDW - LGA
Nonstop2h 10mSouthwest
Deal found 5/29$149
Tue 6/116:00 amLGA - MDW
2 stops16h 20mFrontier
Tue 6/187:00 amMDW - LGA
1 stop12h 59mFrontier
Deal found 5/29$153

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 2,784,634 searches and data were last updated on May 30, 2024.
These are some of the most attractive deals on flights to Chicago in 2024. Check back regularly for other flight deals.
Tue 9/1010:56 amLGA - MDW
1 stop10h 53mFrontier
Sat 9/146:00 amMDW - LGA
1 stop15h 00mFrontier
Deal found 5/29$115
Sat 8/3110:50 pmLGA - MDW
1 stop14h 02mFrontier
Tue 9/39:44 pmMDW - LGA
1 stop11h 22mFrontier
Deal found 5/29$116
Wed 9/2510:56 amLGA - MDW
1 stop10h 53mFrontier
Sat 9/286:00 amMDW - LGA
1 stop15h 00mFrontier
Deal found 5/30$117
Sat 9/144:20 pmLGA - MDW
1 stop5h 29mFrontier
Sat 9/219:44 pmMDW - LGA
1 stop11h 22mFrontier
Deal found 5/29$124
Sat 6/810:50 pmLGA - MDW
1 stop13h 22mFrontier
Mon 6/1012:57 pmMDW - LGA
1 stop9h 18mFrontier
Deal found 5/29$126
Wed 6/510:59 pmLGA - MDW
1 stop23h 46mFrontier
Tue 6/117:00 amMDW - LGA
1 stop12h 59mFrontier
Deal found 5/29$130
Fri 9/64:20 pmLGA - MDW
1 stop5h 29mFrontier
Wed 9/1112:15 pmMDW - LGA
1 stop10h 03mFrontier
Deal found 5/30$134
Tue 6/116:00 amLGA - MDW
2 stops16h 20mFrontier
Wed 6/126:00 amMDW - LGA
1 stop13h 59mFrontier
Deal found 5/29$135
Fri 9/610:50 pmLGA - MDW
1 stop14h 02mFrontier
Sat 9/149:44 pmMDW - LGA
1 stop11h 22mFrontier
Deal found 5/29$136

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 2,784,634 searches and data was last updated on May 30, 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 6/510:59 pmLGA - MDW
1 stop13h 09mFrontier
Wed 6/1212:57 pmMDW - LGA
1 stop9h 46mFrontier
Deal found 5/29$115
Sat 6/810:50 pmLGA - MDW
1 stop13h 22mFrontier
Mon 6/1012:57 pmMDW - LGA
1 stop9h 18mFrontier
Deal found 5/29$126
Wed 6/510:59 pmLGA - MDW
1 stop23h 46mFrontier
Tue 6/117:00 amMDW - LGA
1 stop12h 59mFrontier
Deal found 5/29$130
Sat 6/810:50 pmLGA - MDW
1 stop13h 22mFrontier
Mon 7/15:55 amMDW - LGA
1 stop15h 05mFrontier
Deal found 5/28$143
Sat 6/810:50 pmLGA - MDW
1 stop13h 22mFrontier
Mon 7/17:30 amMDW - LGA
2 stops12h 29mFrontier
Deal found 5/28$148
Tue 6/410:50 pmLGA - MDW
1 stop14h 10mFrontier
Tue 6/116:00 amMDW - LGA
1 stop15h 00mFrontier
Deal found 5/30$157
Sat 6/810:52 amLGA - MDW
1 stop11h 55mFrontier
Tue 6/117:00 amMDW - LGA
1 stop12h 59mFrontier
Deal found 5/29$163
Fri 6/76:00 amLGA - MDW
1 stop17h 58mFrontier
Tue 6/116:00 amMDW - LGA
1 stop15h 00mFrontier
Deal found 5/28$166
Wed 6/56:00 amLGA - MDW
1 stop17h 58mFrontier
Tue 6/116:00 amMDW - LGA
1 stop15h 00mFrontier
Deal found 5/30$171

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 2,784,634 searches and data was last updated on May 30, 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.
Tue 8/204:20 pmLGA - MDW
1 stop5h 50mFrontier
Deal found 5/29$58
Tue 9/104:20 pmLGA - MDW
1 stop5h 29mFrontier
Deal found 5/29$59
Tue 8/274:20 pmLGA - MDW
1 stop5h 50mFrontier
Deal found 5/29$63
Tue 6/1110:50 pmLGA - MDW
1 stop14h 10mFrontier
Deal found 5/29$64
Wed 6/126:00 amLGA - MDW
1 stop17h 58mFrontier
Deal found 5/29$65
Sat 8/314:20 pmLGA - MDW
1 stop6h 32mFrontier
Deal found 5/30$66
Tue 6/1110:50 pmLGA - MDW
1 stop14h 10mFrontier
Deal found 5/30$67
Wed 8/216:00 amLGA - MDW
1 stop16h 55mFrontier
Deal found 5/29$68
Wed 6/510:59 pmLGA - MDW
1 stop13h 09mFrontier
Deal found 5/29$69

Direct flights to Midway Airport

Wed 6/199:45 pmLGA - MDW
Nonstop2h 25mSouthwest
Fri 6/217:55 amMDW - LGA
Nonstop2h 10mSouthwest
Deal found 5/29$149
Mon 7/157:30 pmLGA - MDW
Nonstop2h 40mSouthwest
Wed 7/175:50 pmMDW - LGA
Nonstop2h 10mSouthwest
Deal found 5/29$172
Tue 6/119:50 pmLGA - MDW
Nonstop2h 25mSouthwest
Thu 6/135:55 amMDW - LGA
Nonstop2h 05mSouthwest
Deal found 5/28$221
Tue 6/259:05 amLGA - MDW
Nonstop2h 25mSouthwest
Wed 6/267:55 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 5/29$228
Tue 7/23:35 pmLGA - MDW
Nonstop2h 30mSouthwest
Thu 7/46:00 amMDW - LGA
Nonstop2h 10mSouthwest
Deal found 5/29$236
Tue 6/116:10 amLGA - MDW
Nonstop2h 20mSouthwest
Thu 6/133:45 pmMDW - LGA
Nonstop2h 10mSouthwest
Deal found 5/30$244
Mon 7/299:50 pmLGA - MDW
Nonstop2h 25mSouthwest
Wed 7/315:55 amMDW - LGA
Nonstop2h 05mSouthwest
Deal found 5/30$264
Sat 6/156:30 amLGA - MDW
Nonstop2h 20mSouthwest
Mon 6/178:15 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 5/30$272
Mon 6/109:10 amLGA - MDW
Nonstop2h 25mSouthwest
Thu 6/135:55 amMDW - LGA
Nonstop2h 05mSouthwest
Deal found 5/30$287

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 2,784,634 searches and data was last updated on May 30, 2024.

Fly from

Any airport

Budget

$115 - $305

Route

Depart

Return

Price

New York LaGuardiaChicago Midway

LGA - MDW

LGAMDW

New York LaGuardia

Tue 9/10

1 stop10h 53m

Chicago Midway

Sat 9/14

1 stop15h 00m

$115

New York LaGuardiaChicago Midway

LGA - MDW

LGAMDW

New York LaGuardia

Sat 8/31

1 stop14h 02m

Chicago Midway

Tue 9/3

1 stop11h 22m

$116

New York LaGuardiaChicago Midway

LGA - MDW

LGAMDW

New York LaGuardia

Wed 9/25

1 stop10h 53m

Chicago Midway

Sat 9/28

1 stop15h 00m

$117

New York LaGuardiaChicago Midway

LGA - MDW

LGAMDW

New York LaGuardia

Sat 9/14

1 stop5h 29m

Chicago Midway

Sat 9/21

1 stop11h 22m

$124

New York LaGuardiaChicago Midway

LGA - MDW

LGAMDW

New York LaGuardia

Wed 6/19

Nonstop2h 25m

Chicago Midway

Fri 6/21

Nonstop2h 10m

$149

NewarkChicago Midway

EWR - MDW

EWRMDW

Newark

Tue 9/10

1 stop5h 58m

Chicago Midway

Sat 9/14

1 stop5h 41m

$156

New York LaGuardiaChicago Midway

LGA - MDW

LGAMDW

New York LaGuardia

Wed 6/19

1 stop6h 00m

Chicago Midway

Fri 6/21

Nonstop2h 10m

$158

NewarkChicago Midway

EWR - MDW

EWRMDW

Newark

Fri 6/21

1 stop10h 23m

Chicago Midway

Mon 6/24

1 stop11h 57m

$241

NewarkChicago Midway

EWR - MDW

EWRMDW

Newark

Mon 7/29

1 stop9h 45m

Chicago Midway

Fri 8/2

2 stops19h 29m

$305

Flights are sorted by cheapest first

Deals found on 5/29

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.
Search Deals

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 30, 2024.
To help decide which airline to fly to Chicago, see what other customers have to say about Southwest, Frontier and Delta. 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
5,956 reviews
Check prices

Boarding

8.3

Entertainment

7.8

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

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
5,956 reviews
Southwest
8.2
Very good
5,956 reviews
Check prices

Boarding

8.3

Entertainment

7.8

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

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
10,457 reviews
Southwest
8.2
Very good
5,956 reviews
Check prices

Boarding

8.3

Entertainment

7.8

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

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
2,866 reviews
Southwest
8.2
Very good
5,956 reviews
Check prices

Boarding

8.3

Entertainment

7.8

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

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
1,002 reviews
Southwest
8.2
Very good
5,956 reviews
Check prices

Boarding

8.3

Entertainment

7.8

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

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
394 reviews
Southwest
8.2
Very good
5,956 reviews
Check prices

Boarding

8.3

Entertainment

7.8

Food

7.3

Crew

8.7

Comfort

8.1

Overall

8.2

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, Grand Rapids offers the quickest one-way flight (1 hour 0 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 airports near Midway
Other Chicago travelers fly to these airports near Midway.

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Search flights to Midway by cabin class

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