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$71+ Cheap flights from Indianapolis (IND) to Midway (MDW)

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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
IND — MDW
May 28 — Jun 41
Thu 5/28
Thu 6/4
1 adult, Economy
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Cheap flight deals from Indianapolis to Midway

Cheapest flights from Indianapolis to Midway
Explore the most affordable flight options available from Indianapolis to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 28, 2026.

This Southwest deal was found by Cheapflights users on 4/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:40 am
IND
-
MDW
Nonstop0h 55m
Southwest
Wed 6/38:40 pm
MDW
-
IND
Nonstop1h 10m
Southwest
Deal found 4/27$157
This Southwest deal was found by Cheapflights users on 4/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:40 am
IND
-
MDW
Nonstop0h 55m
Southwest
Thu 5/2810:25 am
MDW
-
IND
Nonstop1h 05m
Southwest
Deal found 4/25$189
This Kiwi.com deal was found by Cheapflights users on 4/27. 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 5/2712:14 pm
IND
-
MDW
1 stop10h 48m
Multiple Airlines
Wed 6/312:04 pm
MDW
-
IND
2 stops22h 17m
Multiple Airlines
Deal found 4/27$196
This Southwest deal was found by Cheapflights users on 4/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/39:35 am
IND
-
MDW
2 stops7h 15m
Southwest
Thu 6/410:00 am
MDW
-
IND
Nonstop1h 05m
Southwest
Deal found 4/25$204
This Southwest deal was found by Cheapflights users on 4/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:35 am
IND
-
MDW
Nonstop0h 55m
Southwest
Mon 5/259:45 pm
MDW
-
IND
Nonstop1h 10m
Southwest
Deal found 4/25$221
This Southwest deal was found by Cheapflights users on 4/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/162:40 pm
IND
-
MDW
Nonstop1h 00m
Southwest
Sat 5/164:20 pm
MDW
-
IND
1 stop3h 40m
Southwest
Deal found 4/25$231

Find flight deals from Indianapolis to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Indianapolis (IND) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$157
(Southwest)

One-way from

$71
(Kiwi.com)

Popular in

January

Cheapest in

September

Average price

$328

Good round-trip deal

$362 or less

Good one-way deal

$193 or less
Provider with most accurate pricing for Indianapolis-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Indianapolis-Chicago Midway flights.
Search Deals
From Indianapolis to Chicago Midway
Search Deals
One-way flight from Indianapolis to Chicago Midway
Search Deals
Highest demand for flights based on searches. 26% potential increase in price ($132 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Indianapolis to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Indianapolis to Chicago Midway.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Indianapolis to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 28, 2026.
Use the filters below to find and compare flights from Indianapolis to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 5/27

6:40 am-6:35 am

Nonstop0h 55m

Chicago Midway

Wed 6/3

8:40 pm-10:50 pm

Nonstop1h 10m

$157

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 6/3

5:10 pm-5:10 pm

Nonstop1h 00m

Chicago Midway

Thu 6/4

10:00 am-12:05 pm

Nonstop1h 05m

$189

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 5/27

9:35 am-4:15 pm

1 stop7h 40m

Chicago Midway

Thu 5/28

9:45 pm-11:55 pm

Nonstop1h 10m

$199

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Sat 5/16

6:30 am-8:43 am

1 stop3h 13m

Chicago Midway

Sat 5/16

1:22 pm-6:53 pm

1 stop4h 31m

$241

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Sat 5/23

6:35 am-6:30 am

Nonstop0h 55m

Chicago Midway

Sun 5/24

6:40 am-1:00 pm

1 stop5h 20m

$279

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Sat 5/23

2:40 pm-2:40 pm

Nonstop1h 00m

Chicago Midway

Sun 5/31

10:05 am-12:15 pm

Nonstop1h 10m

$281

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Thu 5/28

6:50 am-6:45 am

Nonstop0h 55m

Chicago Midway

Fri 5/29

2:10 pm-11:00 pm

2 stops7h 50m

$284

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Sat 5/23

8:10 am-12:42 pm

1 stop5h 32m

Chicago Midway

Sun 5/31

9:22 am-1:27 pm

1 stop3h 05m

$301

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Sat 7/25

4:50 pm-5:00 pm

Nonstop1h 10m

Chicago Midway

Sun 8/2

5:05 am-12:10 pm

1 stop6h 05m

$327
Cheapest one-way

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 5/27

7:02 am-12:42 pm

2 stops6h 40m

$94

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/26

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

Compare providers for flights from Indianapolis to 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 Indianapolis to Midway in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Indianapolis-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Indianapolis-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Indianapolis-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Indianapolis-Chicago Midway Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Indianapolis-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Indianapolis to Midway

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

Cheapflights Insights

Everything you need to know about your flight from Indianapolis to Chicago Midway Airport

What is the cheapest time of day to fly from IND to MDW?

Find hourly flight availability from Indianapolis to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 28, 2026.

It’s typically best to fly out from Indianapolis to Chicago Midway Airport in the afternoon. Doing so could potentially save you 35% on the flight price compared to flying at noon, which is usually more expensive.

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 April 28, 2026.
Get a feel of what it's like to fly with Southwest from Indianapolis to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,314 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,314 reviews
Southwest
8.0
Very good
4,314 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Indianapolis to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Indianapolis to Chicago Midway?

    Indianapolis (IND), located 8.3 mi from the city center, is the airport you fly out of when you book flights from Indianapolis to Chicago Midway. 1 airline have flights from Indianapolis to Chicago Midway on a regular basis. Booking flights from Indianapolis to Chicago Midway should not be difficult; the airport handles an average of 1 outbound flight to Chicago Midway per day.

  • How long is the flight from Indianapolis to Chicago Midway Airport?

    For as low as $157, Southwest can have you in Chicago Midway Airport from Indianapolis in 55m. The distance from Indianapolis to Chicago Midway Airport is about 162 mi. All flights are typically nonstop.

  • What is the cheapest airline to fly from Indianapolis to Chicago Midway Airport round-trip?

    Southwest, at $192, was found to be the cheapest airline from Indianapolis to Chicago Midway Airport.. You may be able to fly from Indianapolis to Chicago Midway Airport for 47% less than the average price by searching for this airline.

  • What are the cheapest flights from Indianapolis to Chicago Midway Airport?

    Looking for the cheapest flight from Indianapolis to Chicago Midway Airport? While on average our users pay $338, our data indicates the cheapest price to be $107. The most popular route (Indianapolis - Chicago Midway), is priced around $189.

  • Can I find deals for flights from Indianapolis to Midway that include hotel bookings?

    Yes. In addition to deals on Indianapolis to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Indianapolis to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Indianapolis to Midway.

  • Can I find deals for business class flights from Indianapolis to Midway?

    Yes. Cheapflights offers flight deals from Indianapolis to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Indianapolis to Midway

Discover the top airline that operate flights from Indianapolis to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$192Average$337FlexibilityNo cancel feeOn-time63%

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