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Cheap flights from Indianapolis to Chicago from $66

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 3/10. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
7:27 pm - 10:25 pm
IND
-
MDW
27h 58m
1 stop
Frontier Logo
6:00 am - 6:31 pm
MDW
-
IND
11h 31m
1 stop
$133Frontier
Thu, Feb 19 - Mon, Feb 23
Multiple Airlines Logo
6:00 am - 1:00 pm
IND
-
MDW
8h 00m
1 stop
Multiple Airlines Logo
7:30 am - 11:22 pm
MDW
-
IND
14h 52m
1 stop
$142Multiple Airlines
Wed, May 6 - Sat, May 9
Multiple Airlines Logo
6:00 am - 1:00 pm
IND
-
MDW
8h 00m
1 stop
Multiple Airlines Logo
7:30 am - 11:22 pm
MDW
-
IND
14h 52m
1 stop
$153Multiple Airlines
Tue, Apr 28 - Sat, May 2
Multiple Airlines Logo
6:00 am - 4:16 pm
IND
-
MDW
35h 16m
2 stops
Multiple Airlines Logo
6:05 am - 11:16 am
MDW
-
IND
28h 11m
1 stop
$157Multiple Airlines
Wed, Mar 4 - Wed, Mar 11
Multiple Airlines Logo
6:00 am - 1:00 pm
IND
-
MDW
8h 00m
1 stop
Multiple Airlines Logo
7:30 am - 11:22 pm
MDW
-
IND
14h 52m
1 stop
$158Multiple Airlines
Mon, Apr 20 - Sat, Apr 25
Multiple Airlines Logo
3:12 pm - 7:07 pm
IND
-
MDW
28h 55m
2 stops
Multiple Airlines Logo
7:30 am - 11:25 pm
MDW
-
IND
14h 55m
1 stop
$160Multiple Airlines
Tue, Mar 3 - Tue, Mar 10
Southwest Logo
6:40 am - 6:35 am
IND
-
MDW
0h 55mnonstop
Southwest Logo
10:00 am - 12:05 pm
MDW
-
IND
1h 05mnonstop
$164Southwest
Tue, Apr 28 - Sat, May 2
Multiple Airlines Logo
12:16 pm - 7:47 pm
IND
-
MDW
8h 31m
1 stop
Multiple Airlines Logo
7:30 am - 11:15 pm
MDW
-
IND
14h 45m
1 stop
$165Multiple Airlines
Sun, Mar 15 - Tue, Mar 17
Frontier Logo
1:23 pm - 2:26 pm
IND
-
MDW
26h 03m
1 stop
Frontier Logo
6:05 am - 11:16 am
MDW
-
IND
28h 11m
1 stop
$169Frontier
Wed, Mar 4 - Wed, Mar 11
Southwest Logo
6:00 pm - 6:00 pm
IND
-
MDW
1h 00mnonstop
Southwest Logo
6:15 pm - 8:20 pm
MDW
-
IND
1h 05mnonstop
$171Southwest
Mon, Apr 20 - Sat, Apr 25

Frontier flights from Indianapolis to Chicago Midway Airport

Our best Frontier deals on Indianapolis to Chicago Midway Airport flight tickets
Frontier
Feb 19
IND7:27 pmIndianapolis
27h 58m
1 stop
MDW10:25 pmChicago Midway
Feb 23
MDW6:00 amChicago Midway
11h 31m
1 stop
IND6:31 pmIndianapolis
$133
Frontier
Mar 4
IND1:23 pmIndianapolis
26h 03m
1 stop
MDW2:26 pmChicago Midway
Mar 11
MDW6:05 amChicago Midway
28h 11m
1 stop
IND11:16 amIndianapolis
$169
Frontier
Apr 16
IND12:12 pmIndianapolis
11h 07m
1 stop
MDW10:19 pmChicago Midway
Apr 19
MDW6:00 amChicago Midway
28h 17m
1 stop
IND11:17 amIndianapolis
$183

Southwest flights from Indianapolis to Chicago Midway Airport

Our best Southwest deals on Indianapolis to Chicago Midway Airport flight tickets
Southwest
Apr 28
IND6:40 amIndianapolis
0h 55m
MDW6:35 amChicago Midway
May 2
MDW10:00 amChicago Midway
1h 05m
IND12:05 pmIndianapolis
$164
Southwest
Apr 20
IND6:00 pmIndianapolis
1h 00m
MDW6:00 pmChicago Midway
Apr 25
MDW6:15 pmChicago Midway
1h 05m
IND8:20 pmIndianapolis
$171
Southwest
May 6
IND6:40 amIndianapolis
0h 55m
MDW6:35 amChicago Midway
May 9
MDW7:45 amChicago Midway
3h 20m
1 stop
IND12:05 pmIndianapolis
$174

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 February 6, 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

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Thu 2/19

7:27 pm-10:25 pm

1 stop27h 58m

Chicago Midway

Mon 2/23

6:00 am-6:31 pm

1 stop11h 31m

$133

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 5/6

6:00 am-1:00 pm

1 stop8h 00m

Chicago Midway

Sat 5/9

7:30 am-11:22 pm

1 stop14h 52m

$142

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Tue 4/28

6:00 am-1:00 pm

1 stop8h 00m

Chicago Midway

Sat 5/2

7:30 am-11:22 pm

1 stop14h 52m

$153

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 3/4

6:00 am-4:16 pm

2 stops35h 16m

Chicago Midway

Wed 3/11

6:05 am-11:16 am

1 stop28h 11m

$157

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Mon 4/20

6:00 am-1:00 pm

1 stop8h 00m

Chicago Midway

Sat 4/25

7:30 am-11:22 pm

1 stop14h 52m

$158

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Tue 3/3

3:12 pm-7:07 pm

2 stops28h 55m

Chicago Midway

Tue 3/10

7:30 am-11:25 pm

1 stop14h 55m

$160

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Tue 4/28

6:40 am-6:35 am

Nonstop0h 55m

Chicago Midway

Sat 5/2

10:00 am-12:05 pm

Nonstop1h 05m

$164

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Sun 3/15

12:16 pm-7:47 pm

1 stop8h 31m

Chicago Midway

Tue 3/17

7:30 am-11:15 pm

1 stop14h 45m

$165

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 3/4

1:23 pm-2:26 pm

1 stop26h 03m

Chicago Midway

Wed 3/11

6:05 am-11:16 am

1 stop28h 11m

$169

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Mon 4/20

6:00 pm-6:00 pm

Nonstop1h 00m

Chicago Midway

Sat 4/25

6:15 pm-8:20 pm

Nonstop1h 05m

$171

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 day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Indianapolis. The lowest ticket price found for a Tuesday departure recently was $332. 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, Friday 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 $426.

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 $361 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $456. 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

What cabin class options are available on Indianapolis to Chicago Midway flights?

There is only 1 cabin class available to choose from on Indianapolis to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

$203

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 $203. The best round-trip flight deal from Indianapolis to Chicago Midway Airport found on momondo in the last 72 hours is $364.
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

  • 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
8.0
4,280 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 7 flights on this route every week with an average price of $337. Southwest is rated 8.0/10 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
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Munster
Crown Point
Chesterton
Monticello
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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