$39 Cheap Flights from Chicago (MDW) to Indianapolis (IND)

View $39 flight on Mon, Sep 22, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Indianapolis (MDW-IND)

Prices were available within the past 7 days and start at $39 for one-way flights and $77 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Mon, Sep 22 - Thu, Sep 25
MDW
Chicago
IND
Indianapolis
$77 Roundtrip, found 1 day ago
$77
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Sep 22 from Chicago to Indianapolis, returning Thu, Sep 25, priced at $77 found 1 day ago
Southwest Airlines
Thu, Jul 31 - Tue, Aug 12
MDW
Chicago
IND
Indianapolis
$87 Roundtrip, found 16 hours ago
$87
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Thu, Jul 31 from Chicago to Indianapolis, returning Tue, Aug 12, priced at $87 found 16 hours ago
Southwest Airlines
Thu, Jul 31 - Tue, Aug 12
MDW
Chicago
IND
Indianapolis
$97 Roundtrip, found 16 hours ago
$97
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Thu, Jul 31 from Chicago to Indianapolis, returning Tue, Aug 12, priced at $97 found 16 hours ago
Southwest Airlines
Mon, Sep 22 - Thu, Sep 25
MDW
Chicago
IND
Indianapolis
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Sep 22 from Chicago to Indianapolis, returning Thu, Sep 25, priced at $117 found 1 day ago
Southwest Airlines
Thu, Jul 31 - Tue, Aug 12
MDW
Chicago
IND
Indianapolis
$127 Roundtrip, found 16 hours ago
$127
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Thu, Jul 31 from Chicago to Indianapolis, returning Tue, Aug 12, priced at $127 found 16 hours ago
Southwest Airlines
Sat, Aug 23 - Tue, Aug 26
MDW
Chicago
IND
Indianapolis
$128 Roundtrip, found 22 hours ago
$128
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Sat, Aug 23 from Chicago to Indianapolis, returning Tue, Aug 26, priced at $128 found 22 hours ago
Southwest Airlines
Thu, Jul 31 - Tue, Aug 12
MDW
Chicago
IND
Indianapolis
$137 Roundtrip, found 16 hours ago
$137
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Thu, Jul 31 from Chicago to Indianapolis, returning Tue, Aug 12, priced at $137 found 16 hours ago
Southwest Airlines
Sat, Aug 23 - Tue, Aug 26
MDW
Chicago
IND
Indianapolis
$138 Roundtrip, found 22 hours ago
$138
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Sat, Aug 23 from Chicago to Indianapolis, returning Tue, Aug 26, priced at $138 found 22 hours ago
Southwest Airlines
Sat, Aug 23 - Tue, Aug 26
MDW
Chicago
IND
Indianapolis
$142 Roundtrip, found 22 hours ago
$142
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Sat, Aug 23 from Chicago to Indianapolis, returning Tue, Aug 26, priced at $142 found 22 hours ago
Delta
Wed, May 7 - Wed, May 14
MDW
Chicago
IND
Indianapolis
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, May 7 from Chicago to Indianapolis, returning Wed, May 14, priced at $158 found 1 day ago

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Indianapolis Intl. Airport (IND) cost?
Discover the latest flight deals from MDW to IND by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to IND?
The cheapest flights from MDW to IND are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Indianapolis Intl. Airport (IND)?
You can’t catch a direct flight from Chicago, IL (MDW-Midway Intl.) to Indianapolis Intl. Airport (IND). However, you can arrive in Indianapolis without any layovers by leaving from O’Hare Intl. Airport (ORD).
What is the cheapest airline that flies from MDW to IND?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from MDW to IND. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Indianapolis Intl. Airport (IND)?
Direct flights from Midway Intl. Airport (MDW) to Indianapolis Intl. Airport (IND) aren’t available daily, so you’ll need to take a flight with a layover. Explore your options with Expedia’s filter tool. Enter your dates and pick either “1 Stop” or “2+ Stops.”
What day of the week has the most flights from MDW to IND?
Friday is generally the busiest day for flights, while Tuesday tends to be the quietest.* Remember that flight schedules can change depending on a number of factors, including the season and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Indianapolis Intl. Airport (IND)?
Book a flight from Midway Intl. Airport (MDW) to Indianapolis Intl. Airport (IND) that leaves before 3 PM to reduce the risk of delays and cancellations. Departures after this time have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Indianapolis Intl. Airport (IND) last-minute?
Last-minute bookings from MDW to IND are usually more expensive. To secure the best rates, start looking for flights early. That said, if you’re flexible with your travel dates, it’s possible to find a cheap fare right before your trip.
Is it cheaper to book a MDW to IND flight and hotel package?
Compared with arranging flights and hotels separately, booking a MDW to IND flight and hotel package with Expedia could lead to significant savings. Better still, having everything in one convenient place takes the hassle out of planning your trip. Simply secure your flights and select from our extensive range of hotels, then tailor your trip with extras like activities and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Indianapolis Intl. Airport (IND)?
If you reserved your MDW to IND flight in the last 24 hours, you may be able to modify or cancel it at no cost. Depending on the airline and the ticket type you purchased, additional charges may apply for changes after that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for further details.
*Available to One Key members.