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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 10/14. 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

Southwest Logo
6:25 am - 6:30 amIND-MDW
1h 05mnonstop
Southwest Logo
9:45 am - 11:45 amMDW-IND
1h 00mnonstop
$158Southwest
Find Deal
Tue, Oct 7 - Thu, Oct 9
Frontier Logo
12:06 pm - 4:00 pmIND-MDW
4h 54m1 stop
Frontier Logo
9:48 am - 5:21 pmMDW-IND
6h 33m1 stop
$159Frontier
Find Deal
Mon, Sep 29 - Fri, Oct 3
Frontier Logo
3:34 pm - 11:20 pmIND-MDW
8h 46m1 stop
Frontier Logo
12:30 pm - 7:44 pmMDW-IND
6h 14m1 stop
$163Frontier
Find Deal
Mon, Oct 20 - Fri, Nov 14
Frontier Logo
10:14 pm - 10:26 amIND-MDW
13h 12m1 stop
Frontier Logo
9:27 am - 9:19 pmMDW-IND
10h 52m1 stop
$165Frontier
Find Deal
Fri, Nov 14 - Mon, Nov 17
Frontier Logo
12:06 pm - 4:00 pmIND-MDW
4h 54m1 stop
Frontier Logo
8:19 am - 5:10 pmMDW-IND
7h 51m1 stop
$173Frontier
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Fri, Sep 26 - Mon, Sep 29
Southwest Logo
6:25 am - 6:30 amIND-MDW
1h 05mnonstop
Southwest Logo
6:00 am - 1:35 pmMDW-IND
6h 35m1 stop
$178Southwest
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Tue, Oct 7 - Thu, Oct 9
Southwest Logo
6:25 am - 6:30 amIND-MDW
1h 05mnonstop
Southwest Logo
6:00 am - 1:25 pmMDW-IND
6h 25m2 stops
$183Southwest
Find Deal
Tue, Oct 7 - Thu, Oct 9
Southwest Logo
5:00 pm - 5:10 pmIND-MDW
1h 10mnonstop
Southwest Logo
10:00 am - 12:05 pmMDW-IND
1h 05mnonstop
$191Southwest
Find Deal
Wed, Nov 5 - Wed, Mar 25
Delta Logo
6:30 am - 8:40 amIND-MDW
3h 10m1 stop
Delta Logo
11:10 am - 5:26 pmMDW-IND
5h 16m1 stop
$238Delta
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Wed, Nov 5 - Sat, Nov 8
Delta Logo
11:41 am - 4:25 pmIND-MDW
5h 44m1 stop
Delta Logo
9:30 am - 1:32 pmMDW-IND
3h 02m1 stop
$265Delta
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Tue, Mar 10 - Wed, Mar 11

Southwest flights from Indianapolis to Chicago Midway Airport

Our best Southwest deals on Indianapolis to Chicago Midway Airport flight tickets
Southwest
Oct 7
IND6:25 amIndianapolis
1h 05m
MDW6:30 amChicago Midway
Oct 9
MDW9:45 amChicago Midway
1h 00m
IND11:45 amIndianapolis
$158
Find similar
Southwest
Oct 7
IND6:25 amIndianapolis
1h 05m
MDW6:30 amChicago Midway
Oct 9
MDW6:00 amChicago Midway
6h 35m
1 stop
IND1:35 pmIndianapolis
$178
Find similar
Southwest
Oct 7
IND6:25 amIndianapolis
1h 05m
MDW6:30 amChicago Midway
Oct 9
MDW6:00 amChicago Midway
6h 25m
2 stops
IND1:25 pmIndianapolis
$183
Find similar

Delta flights from Indianapolis to Chicago Midway Airport

Our best Delta deals on Indianapolis to Chicago Midway Airport flight tickets
Delta
Nov 5
IND6:30 amIndianapolis
3h 10m
1 stop
MDW8:40 amChicago Midway
Nov 8
MDW11:10 amChicago Midway
5h 16m
1 stop
IND5:26 pmIndianapolis
$238
Find similar
Delta
Mar 10
IND11:41 amIndianapolis
5h 44m
1 stop
MDW4:25 pmChicago Midway
Mar 11
MDW9:30 amChicago Midway
3h 02m
1 stop
IND1:32 pmIndianapolis
$265
Find similar
Delta
Mar 10
IND7:50 amIndianapolis
11h 18m
2 stops
MDW6:08 pmChicago Midway
Mar 11
MDW9:30 amChicago Midway
3h 02m
1 stop
IND1:32 pmIndianapolis
$270
Find similar

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 September 15, 2025.
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

Tue 10/7

6:25 am-6:30 am

Nonstop1h 05m

Chicago Midway

Thu 10/9

9:45 am-11:45 am

Nonstop1h 00m

$158

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Mon 9/29

12:06 pm-4:00 pm

1 stop4h 54m

Chicago Midway

Fri 10/3

9:48 am-5:21 pm

1 stop6h 33m

$159

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Mon 10/20

3:34 pm-11:20 pm

1 stop8h 46m

Chicago Midway

Fri 11/14

12:30 pm-7:44 pm

1 stop6h 14m

$163

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Fri 11/14

10:14 pm-10:26 am

1 stop13h 12m

Chicago Midway

Mon 11/17

9:27 am-9:19 pm

1 stop10h 52m

$165

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Fri 9/26

12:06 pm-4:00 pm

1 stop4h 54m

Chicago Midway

Mon 9/29

8:19 am-5:10 pm

1 stop7h 51m

$173

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Tue 10/7

6:25 am-6:30 am

Nonstop1h 05m

Chicago Midway

Thu 10/9

6:00 am-1:35 pm

1 stop6h 35m

$178

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Tue 10/7

6:25 am-6:30 am

Nonstop1h 05m

Chicago Midway

Thu 10/9

6:00 am-1:25 pm

2 stops6h 25m

$183

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 11/5

5:00 pm-5:10 pm

Nonstop1h 10m

Chicago Midway

Wed 3/25

10:00 am-12:05 pm

Nonstop1h 05m

$191

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Wed 11/5

6:30 am-8:40 am

1 stop3h 10m

Chicago Midway

Sat 11/8

11:10 am-5:26 pm

1 stop5h 16m

$238

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Tue 3/10

11:41 am-4:25 pm

1 stop5h 44m

Chicago Midway

Wed 3/11

9:30 am-1:32 pm

1 stop3h 02m

$265

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, Wednesday is the cheapest day to fly to Chicago Midway Airport from Indianapolis. The lowest ticket price found for a Wednesday departure recently was $258. 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, Sunday 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 $363.

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 $310 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $328. 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?

You could potentially save up to 6% on your flight if you consider stops on a Indianapolis to Chicago Midway Airport flight.

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

$157

Fastest flight time

1h 00m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Indianapolis in the past 72 hours is $157. The best round-trip flight deal from Indianapolis to Chicago Midway Airport found on momondo in the last 72 hours is $260.
The fastest flight from Indianapolis to Chicago Midway Airport takes 1h 00m
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 1h 05m.

  • 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 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?

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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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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