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Cheap flights from Indianapolis to Chicago from $69

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Indianapolis to Chicago departing on 5/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Indianapolis to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:10 pm - 5:10 pm
IND
-
MDW
1h 00mnonstop
Southwest Logo
9:20 pm - 11:25 pm
MDW
-
IND
1h 05mnonstop
$157Southwest
Wed, Jun 3 - Wed, Jun 10
Southwest Logo
11:05 am - 3:05 pm
IND
-
MDW
5h 00m
1 stop
Southwest Logo
9:20 pm - 11:25 pm
MDW
-
IND
1h 05mnonstop
$167Southwest
Wed, Jun 3 - Wed, Jun 10
Southwest Logo
6:40 am - 6:35 am
IND
-
MDW
0h 55mnonstop
Southwest Logo
11:25 am - 9:55 pm
MDW
-
IND
9h 30m
2 stops
$172Southwest
Tue, Jun 2 - Tue, Jun 9
Southwest Logo
5:10 pm - 5:10 pm
IND
-
MDW
1h 00mnonstop
Southwest Logo
10:10 am - 12:10 pm
MDW
-
IND
1h 00mnonstop
$177Southwest
Wed, Jun 3 - Wed, Jun 10
Southwest Logo
9:35 am - 4:15 pm
IND
-
MDW
7h 40m
1 stop
Southwest Logo
11:25 am - 9:55 pm
MDW
-
IND
9h 30m
2 stops
$182Southwest
Tue, Jun 2 - Tue, Jun 9
Southwest Logo
5:50 am - 10:40 am
IND
-
MDW
5h 50m
1 stop
Southwest Logo
9:20 pm - 11:25 pm
MDW
-
IND
1h 05mnonstop
$187Southwest
Tue, Jun 2 - Tue, Jun 9
Southwest Logo
7:10 am - 3:45 pm
IND
-
MDW
9h 35m
2 stops
Southwest Logo
5:30 pm - 11:10 pm
MDW
-
IND
4h 40m
1 stop
$188Southwest
Wed, Jun 3 - Wed, Jun 10
Southwest Logo
2:40 pm - 2:40 pm
IND
-
MDW
1h 00mnonstop
Southwest Logo
10:00 am - 12:05 pm
MDW
-
IND
1h 05mnonstop
$189Southwest
Sat, May 23 - Tue, Jun 2
Southwest Logo
6:40 am - 6:35 am
IND
-
MDW
0h 55mnonstop
Southwest Logo
11:25 am - 9:55 pm
MDW
-
IND
9h 30m
2 stops
$192Southwest
Tue, Jun 2 - Tue, Jun 9
Southwest Logo
7:10 am - 2:55 pm
IND
-
MDW
8h 45m
2 stops
Southwest Logo
11:25 am - 9:55 pm
MDW
-
IND
9h 30m
2 stops
$193Southwest
Tue, Jun 2 - Tue, Jun 9

Southwest flights from Indianapolis to Chicago Midway Airport

Our best Southwest deals on Indianapolis to Chicago Midway Airport flight tickets
Southwest
Jun 3
IND5:10 pmIndianapolis
1h 00m
MDW5:10 pmChicago Midway
Jun 10
MDW9:20 pmChicago Midway
1h 05m
IND11:25 pmIndianapolis
$157
Southwest
Jun 3
IND11:05 amIndianapolis
5h 00m
1 stop
MDW3:05 pmChicago Midway
Jun 10
MDW9:20 pmChicago Midway
1h 05m
IND11:25 pmIndianapolis
$167
Southwest
Jun 16
IND4:50 pmIndianapolis
1h 10m
MDW5:00 pmChicago Midway
Jun 23
MDW7:50 amChicago Midway
7h 25m
2 stops
IND4:15 pmIndianapolis
$172

Delta flights from Indianapolis to Chicago Midway Airport

Our best Delta deals on Indianapolis to Chicago Midway Airport flight tickets
Delta
Jun 3
IND6:30 amIndianapolis
3h 13m
1 stop
MDW8:43 amChicago Midway
Jun 4
MDW9:22 amChicago Midway
3h 05m
1 stop
IND1:27 pmIndianapolis
$209
Delta
Jun 3
IND8:10 amIndianapolis
5h 32m
1 stop
MDW12:42 pmChicago Midway
Jun 4
MDW9:22 amChicago Midway
3h 05m
1 stop
IND1:27 pmIndianapolis
$219
Delta
Jun 3
IND8:10 amIndianapolis
5h 32m
1 stop
MDW12:42 pmChicago Midway
Jun 4
MDW9:22 amChicago Midway
3h 05m
1 stop
IND1:27 pmIndianapolis
$229

momondo Fare Finder

 
Customize your flight search to find flights from Indianapolis to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated May 7, 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

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 6/3

5:10 pm-5:10 pm

Nonstop1h 00m

Chicago Midway

Wed 6/10

9:20 pm-11:25 pm

Nonstop1h 05m

$157

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 6/3

11:05 am-3:05 pm

1 stop5h 00m

Chicago Midway

Wed 6/10

9:20 pm-11:25 pm

Nonstop1h 05m

$167

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Tue 6/2

6:40 am-6:35 am

Nonstop0h 55m

Chicago Midway

Tue 6/9

11:25 am-9:55 pm

2 stops9h 30m

$172
Quickest round-trip

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 6/3

5:10 pm-5:10 pm

Nonstop1h 00m

Chicago Midway

Wed 6/10

10:10 am-12:10 pm

Nonstop1h 00m

$177

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Tue 6/2

9:35 am-4:15 pm

1 stop7h 40m

Chicago Midway

Tue 6/9

11:25 am-9:55 pm

2 stops9h 30m

$182

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Tue 6/2

5:50 am-10:40 am

1 stop5h 50m

Chicago Midway

Tue 6/9

9:20 pm-11:25 pm

Nonstop1h 05m

$187

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 6/3

7:10 am-3:45 pm

2 stops9h 35m

Chicago Midway

Wed 6/10

5:30 pm-11:10 pm

1 stop4h 40m

$188

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Sat 5/23

2:40 pm-2:40 pm

Nonstop1h 00m

Chicago Midway

Tue 6/2

10:00 am-12:05 pm

Nonstop1h 05m

$189

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Tue 6/2

6:40 am-6:35 am

Nonstop0h 55m

Chicago Midway

Tue 6/9

11:25 am-9:55 pm

2 stops9h 30m

$192

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Tue 6/2

7:10 am-2:55 pm

2 stops8h 45m

Chicago Midway

Tue 6/9

11:25 am-9:55 pm

2 stops9h 30m

$193

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Indianapolis to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of May is, on average, the cheapest month to fly to Chicago Midway Airport from Indianapolis, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of May, then departing from Indianapolis during the month March is also very affordable. Most momondo users find prices during this month for around $0.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Indianapolis. The lowest ticket price found for a Wednesday departure recently was $353. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Saturday is the most expensive day to depart from Indianapolis because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $423.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Indianapolis in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $383 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $595. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Indianapolis to Chicago Midway flight route?

Fly from Indianapolis to Chicago Midway for the best Indianapolis - Chicago Midway flight prices

Can stopping save me money on Indianapolis to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Indianapolis to Chicago Midway Airport.

When to book flights from Indianapolis to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Indianapolis to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Indianapolis to Chicago Midway Airport (IND to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Indianapolis to Chicago Midway Airport

Best Price Found

$193

Fastest flight time

0h 55m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Indianapolis in the past 72 hours is $193. The best round-trip flight deal from Indianapolis to Chicago Midway Airport found on momondo in the last 72 hours is $372.
The fastest flight from Indianapolis to Chicago Midway Airport takes 0h 55m
Direct flights go from Indianapolis to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Indianapolis to Chicago Midway Airport

  • How far is Indianapolis to Chicago Midway by plane?

    A flight from Indianapolis to Chicago Midway will travel around 162.2 mi. In terms of flight time, this usually takes a little over 0h 55m.

  • When did momondo last update prices for flights from Indianapolis Airport to Chicago Midway Airport?

    Prices for flights from Indianapolis Airport to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Indianapolis Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Indianapolis Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Indianapolis Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Indianapolis to Chicago Midway Airport?

  • What is the most popular airline from Indianapolis to Chicago Midway Airport?

Best airlines flying from Indianapolis to Chicago Midway Airport

Compare and see reviews for airlines that fly from Indianapolis to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $192Free CancellationRating
7.9
4,301 reviews
Search Southwest flights

  • Southwest Flights From Indianapolis to Chicago Midway Airport

    The lowest priced Southwest flight from Indianapolis to Chicago Midway Airport from the last 72 hours was $192. Generally, Southwest has 10 flights on this route every week with an average price of $337. Southwest is rated 7.9/10 by our users.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Indianapolis to Chicago?

Finding the right flight to Chicago from Indianapolis is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Indianapolis to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Indianapolis with this policy.

How can momondo help me find flights from Indianapolis to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Indianapolis to Chicago.

I’m not ready to book a flight from Indianapolis to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Indianapolis to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago Midway Airport trip

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