PIT - MDW

$122 Find Cheap Flights from Pittsburgh to Chicago Midway Airport - Compare and Save

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Everything you should know

Cheapest round-trip
$253
Typical prices: $249-$481
Southwest
Sat 11/17Mon 11/19
PIT - MDW • 1 stop
Cheapest non-stop
$263
Typical prices: $251-$483
Southwest
Tue 11/20Fri 11/23
PIT - MDW • Non-stop
Nonstop flights
Every day
You can fly direct with Southwest. Average duration is 1h 34m
Direct flights
+1
Direct flights
+1
Avoid delays
Southwest
Most punctual • 84% on-time
Night
Best time • Fewest delays
Insights
Insights
When to book
25 weeks
in advance
Our data shows that travelers who book at least 25 weeks in advance save around 76% compared to booking last minute.
Insights
Insights
When to travel
November
Cheapest • 17% price drop
April
Most popular
Good to know
+1
Good to know
+1
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We hope you love your trip to Chicago Midway Airport!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Pittsburgh to Midway (PIT-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Pittsburgh to Midway

Tue, Nov 17 - Thu, Nov 19
Southwest Logo
4:00 pm - 9:30 pmPIT  Pittsburgh-MDW Chicago Midway
6h 30m1 stop Baltimore/Washington
Southwest Logo
6:10 pm - 8:45 pmMDW  Chicago Midway-PIT Pittsburgh
1h 35mnonstop
$253Southwest
Thu, Dec 10 - Thu, Dec 17
Southwest Logo
8:25 am - 9:00 amPIT  Pittsburgh-MDW Chicago Midway
1h 35mnonstop
Southwest Logo
4:00 pm - 11:25 pmMDW  Chicago Midway-PIT Pittsburgh
6h 25m1 stop Nashville Intl
$253Southwest
Sat, Dec 5 - Mon, Dec 7
Southwest Logo
2:20 pm - 7:35 pmPIT  Pittsburgh-MDW Chicago Midway
6h 15m1 stop Nashville Intl
Southwest Logo
8:15 am - 10:40 amMDW  Chicago Midway-PIT Pittsburgh
1h 25mnonstop
$253Southwest
Thu, Dec 10 - Mon, Dec 14
Southwest Logo
6:30 pm - 9:35 pmPIT  Pittsburgh-MDW Chicago Midway
4h 05m1 stop Lambert-St Louis
Southwest Logo
6:10 pm - 8:45 pmMDW  Chicago Midway-PIT Pittsburgh
1h 35mnonstop
$253Southwest
Sat, Dec 5 - Mon, Dec 7
Southwest Logo
2:20 pm - 7:35 pmPIT  Pittsburgh-MDW Chicago Midway
6h 15m1 stop Nashville Intl
Southwest Logo
8:15 am - 10:40 amMDW  Chicago Midway-PIT Pittsburgh
1h 25mnonstop
$253Southwest
Thu, Dec 10 - Mon, Dec 14
Southwest Logo
7:25 pm - 7:55 pmPIT  Pittsburgh-MDW Chicago Midway
1h 30mnonstop
Southwest Logo
11:30 am - 9:05 pmMDW  Chicago Midway-PIT Pittsburgh
8h 35m2 stops Lambert-St Louis Nashville Intl
$258Southwest
Sat, Dec 5 - Mon, Dec 7
Southwest Logo
8:45 am - 9:15 amPIT  Pittsburgh-MDW Chicago Midway
1h 30mnonstop
Southwest Logo
7:35 am - 5:55 pmMDW  Chicago Midway-PIT Pittsburgh
9h 20m2 stops Lambert-St Louis Baltimore/Washington
$258Southwest
Tue, Nov 17 - Thu, Nov 19
Southwest Logo
12:20 pm - 7:45 pmPIT  Pittsburgh-MDW Chicago Midway
8h 25m2 stops Baltimore/Washington Buffalo
Southwest Logo
8:15 am - 10:40 amMDW  Chicago Midway-PIT Pittsburgh
1h 25mnonstop
$258Southwest
Thu, Dec 10 - Sun, Dec 13
Frontier Logo
6:28 pm - 5:16 pmPIT  Pittsburgh-MDW Chicago Midway
23h 48m1 stop Orlando
Frontier Logo
8:37 pm - 5:33 pmMDW  Chicago Midway-PIT Pittsburgh
19h 56m1 stop Orlando
$274Frontier
Sat, Dec 12 - Thu, Jan 7
Frontier Logo
6:28 pm - 7:42 pmPIT  Pittsburgh-MDW Chicago Midway
26h 14m1 stop Orlando
Frontier Logo
8:30 pm - 12:49 pmMDW  Chicago Midway-PIT Pittsburgh
15h 19m1 stop Orlando
$279Frontier
Booking Insights

Price, demand and travel trends for Pittsburgh to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Pittsburgh to Chicago Midway Airport?

Round-trip flights from Pittsburgh to Chicago Midway Airport typically range from $249 to $481. The lowest price found in the past 5 days was $253, on Southwest.

What's the cheapest day of the week to fly from Pittsburgh to Chicago Midway Airport?

Based on deals KAYAK users found in the last 12 months, Wednesday is the cheapest day of the week to fly from Pittsburgh to Chicago Midway Airport. It’s 24% cheaper than the average day, while Sunday is the most expensive, with prices 45% higher.

What’s the cheapest month to fly from Pittsburgh to Chicago Midway Airport?

•November is the cheapest month to fly from Pittsburgh to Chicago Midway Airport at $280 round-trip.
•December ($387) and February ($372) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 38% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Pittsburgh to Chicago Midway Airport the cheapest?

Flights from Pittsburgh to Chicago Midway Airport are cheapest 25 weeks before departure. Booking in this window typically costs about 76% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

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Expert advice

Expert advice for your flight from Pittsburgh to Midway

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Matt Meltzer

Matt Meltzer

Expert on PIT

Matt Meltzer has been a travel writer for over a decade, covering U.S. domestic locations and hotels for Thrillist, Fifty Grande, Matador Network, Conde Nast Traveler, and other top publications. He's won multiple travel journalism awards from the Society of American Travel Writers and North American Travel Journalists Association, and currently resides in South Florida.

Read more

Key details for Pittsburgh to Chicago Midway Airport flights

Low season

January

Cheapest flight

$122
Beat the crowds with an average 46% drop in travelers.
The most popular month to fly with an average 25% increase in travelers.
One-way flight from Pittsburgh to Chicago Midway Airport

When to book flights from Pittsburgh to Midway

Are your dates flexible? Find out the best times to travel from Pittsburgh to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Pittsburgh to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Pittsburgh to Chicago Midway Airport?

    These are the earliest and latest flight times available from Pittsburgh to Chicago Midway Airport:

    • Earliest: departs at 7:25 am and lands at 8:59 am
    • Latest: departs at 9:15 pm and lands at 10:49 pm.

    The flight takes about 1h 34m.

  • What cabin classes can I book on flights from Pittsburgh to Chicago Midway Airport?

    Only Economy Class is available on flights from Pittsburgh to Chicago Midway Airport.

  • How long is a flight from Pittsburgh to Chicago Midway Airport?

    A nonstop flight from Pittsburgh to Chicago Midway Airport takes 1h 34m, covering 400 miles.

  • Do I need a passport to fly from Pittsburgh to Chicago Midway Airport?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Pittsburgh to Chicago Midway Airport flight?

    Round-trip flights from Pittsburgh to Chicago Midway Airport range from $249 to $481, with an average of $335 over the past 12 months. Anything below $249 counts as a good deal.

  • How expensive are last-minute Pittsburgh to Chicago Midway Airport flights?

    Last-minute fares on this route (booked within two weeks of departure) run 80% above the $335 route average. Book 25 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Pittsburgh to Chicago Midway Airport?

    On this route, nonstop and layover fares are close on average, with nonstop at $337 round-trip and layover options via Detroit Metropolitan Wayne County (DTW) at $333.

  • How does on-time performance compare across airlines flying from Pittsburgh to Chicago Midway Airport?

    Southwest is the only airline operating Pittsburgh to Chicago Midway Airport flights. 84% of its flights are on time.

  • What is the standard checked-bag allowance on flights from Pittsburgh to Chicago Midway Airport?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • Which aircraft model is used most often on flights from Pittsburgh to Chicago Midway Airport?

    The Airbus A320-100/200 family is used most often on this route, operated mainly by United Airlines and American Airlines. Other aircraft seen on the route include Airbus A319 variants.

  • How are flight departures from Pittsburgh to Chicago Midway Airport spread across the day?

    Morning is the busiest departure period on Pittsburgh to Chicago Midway Airport flights, with 34% of flights leaving in that window. Afternoon departures account for 33%, evening flights for 33%, and night flights for 0%.

  • Have flight prices from Pittsburgh to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $253 to $894. That means the highest observed fare was about 4x higher than the lowest one.

  • How are flight prices from Pittsburgh to Chicago Midway Airport looking right now?

    One-way fares from Pittsburgh to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $131, which is 30% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from Pittsburgh to Chicago Midway Airport?

    Flights from Pittsburgh to Chicago Midway Airport usually depart from Pittsburgh (PIT) and arrive at Chicago Midway (MDW).

  • What time of day has the fewest delays on flights from Pittsburgh to Chicago Midway Airport?

    Night flights have the fewest delays on this route, while evening departures tend to have the most.

  • At what point is a flight considered delayed from Pittsburgh to Chicago Midway Airport?

    A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Pittsburgh to Chicago Midway Airport route, 16% of flights were delayed in the past 3 months, with delays averaging 1h 40m.

  • Which airports do connecting flights from Pittsburgh to Chicago Midway Airport pass through?

    Most connecting flights from Pittsburgh to Chicago Midway Airport pass through Detroit Metropolitan Wayne County (DTW), which handles 100% of one-stop traffic on this route.

  • Can I save money by using flexible dates for flights from Pittsburgh to Chicago Midway Airport?

    Yes. Flexible dates can save you up to 48% on flights from Pittsburgh to Chicago Midway Airport. Wednesday is the cheapest departure day at $256 round-trip on average, while Sunday is the most expensive at $488, a difference of $232.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What airlines fly from Pittsburgh to Chicago Midway Airport?

    Only Southwest operates flights between Pittsburgh and Chicago Midway Airport.

  • What is the time difference between Pittsburgh and Chicago Midway Airport?

    Chicago Midway Airport is 1 hour behind Pittsburgh (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Pittsburgh to Chicago Midway Airport flights?

    Among airlines operating Pittsburgh to Chicago Midway Airport flights:

    • Southwest: offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Pittsburgh to Chicago Midway Airport flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • Southwest: a cabin bag and a checked bag in Economy Class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Pittsburgh to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Wednesday departure and avoid flying on Sunday. On this route, Wednesday flights average $256, about $232 less than Sunday fares (48% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 25 weeks before you fly. On this route, that window historically saves about 76% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Pittsburgh to Chicago Midway Airport trip for November. Fares historically average $280 round-trip in that month - typically $107 less than the most expensive month, which is December (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Detroit Metropolitan Wayne County Airport (DTW) can be cheaper than flying direct. The cheapest layover option averages $333 round-trip on this route - about $4 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel Chicago Midway Airport

Prefer to fly direct from Pittsburgh to Chicago Midway Airport?

 
Find which airlines fly direct from Pittsburgh Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Pittsburgh to Chicago Midway

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

Direct returns

Chicago Midway to Pittsburgh

Monday

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Tuesday

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Wednesday

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Thursday

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Friday

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Saturday

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Sunday

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See more direct flights

More options for your flight from Pittsburgh to Midway

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