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Cheap flights from Indiana to Chicago from $72

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Indiana to Chicago departing on 2/14. 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

Enter your travel dates to find the best prices.
Southwest Logo
4:50 pm - 5:10 pm
SDF
-
MDW
1h 20mnonstop
Southwest Logo
6:15 pm - 8:30 pm
MDW
-
SDF
1h 15mnonstop
$143Southwest
Sat, Feb 14 - Sat, Feb 21
Frontier Logo
1:07 pm - 7:47 pm
CVG
-
MDW
7h 40m
1 stop
Frontier Logo
3:00 pm - 12:59 am
MDW
-
CVG
8h 59m
1 stop
$150Frontier
Mon, Feb 23 - Thu, Feb 26
Southwest Logo
6:40 am - 7:05 am
SDF
-
MDW
1h 25mnonstop
Southwest Logo
5:15 am - 12:20 pm
MDW
-
SDF
6h 05m
1 stop
$153Southwest
Sat, Feb 14 - Sat, Feb 21
Southwest Logo
6:30 am - 6:55 am
SDF
-
MDW
1h 25mnonstop
Southwest Logo
7:55 pm - 10:10 pm
MDW
-
SDF
1h 15mnonstop
$157Southwest
Sat, Jan 31 - Mon, Feb 2
Frontier Logo
1:07 pm - 10:37 pm
CVG
-
MDW
10h 30m
1 stop
Frontier Logo
9:22 pm - 2:10 pm
MDW
-
CVG
15h 48m
1 stop
$159Frontier
Thu, Feb 19 - Mon, Feb 23
Southwest Logo
6:40 am - 7:05 am
SDF
-
MDW
1h 25mnonstop
Southwest Logo
6:50 am - 4:15 pm
MDW
-
SDF
8h 25m
2 stops
$159Southwest
Sat, Feb 14 - Sat, Feb 21
Southwest Logo
6:30 am - 6:55 am
SDF
-
MDW
1h 25mnonstop
Southwest Logo
5:15 pm - 10:45 pm
MDW
-
SDF
4h 30m
1 stop
$167Southwest
Sat, Jan 31 - Mon, Feb 2
Southwest Logo
4:25 pm - 9:50 pm
SDF
-
MDW
6h 25m
1 stop
Southwest Logo
2:10 pm - 9:35 pm
MDW
-
SDF
6h 25m
2 stops
$168Southwest
Sat, Feb 14 - Sat, Feb 21
Delta Logo
8:12 am - 12:46 pm
FWA
-
MDW
5h 34m
1 stop
Delta Logo
9:33 am - 1:29 pm
MDW
-
FWA
2h 56m
1 stop
$199Delta
Sat, Feb 7 - Tue, Feb 10
Delta Logo
7:00 am - 11:05 am
FWA
-
MDW
5h 05m
1 stop
Delta Logo
9:33 am - 1:29 pm
MDW
-
FWA
2h 56m
1 stop
$200Delta
Sat, Jan 31 - Sun, Feb 1

Southwest flights from Indiana to Chicago Midway Airport

Our best Southwest deals on Indiana to Chicago Midway Airport flight tickets
Southwest
Feb 14
SDF4:50 pmLouisville Intl
1h 20m
MDW5:10 pmChicago Midway
Feb 21
MDW6:15 pmChicago Midway
1h 15m
SDF8:30 pmLouisville Intl
$143
Southwest
Feb 14
SDF6:40 amLouisville Intl
1h 25m
MDW7:05 amChicago Midway
Feb 21
MDW5:15 amChicago Midway
6h 05m
1 stop
SDF12:20 pmLouisville Intl
$153
Southwest
Jan 31
SDF6:30 amLouisville Intl
1h 25m
MDW6:55 amChicago Midway
Feb 2
MDW7:55 pmChicago Midway
1h 15m
SDF10:10 pmLouisville Intl
$157

Delta flights from Indiana to Chicago Midway Airport

Our best Delta deals on Indiana to Chicago Midway Airport flight tickets
Delta
Jan 31
SDF5:35 amLouisville Intl
5h 18m
1 stop
MDW9:53 amChicago Midway
Feb 2
MDW6:14 pmChicago Midway
4h 36m
1 stop
SDF11:50 pmLouisville Intl
$191
Delta
Jan 31
SDF6:23 amLouisville Intl
5h 42m
1 stop
MDW11:05 amChicago Midway
Feb 2
MDW1:26 pmChicago Midway
6h 30m
2 stops
SDF8:56 pmLouisville Intl
$196
Delta
Feb 7
FWA8:12 amFort Wayne
5h 34m
1 stop
MDW12:46 pmChicago Midway
Feb 10
MDW9:33 amChicago Midway
2h 56m
1 stop
FWA1:29 pmFort Wayne
$199

momondo Fare Finder

 
Customize your flight search to find flights from Indiana 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 January 12, 2026.
Use the filters below to find and compare flights from Indiana to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 2/14

4:50 pm-5:10 pm

Nonstop1h 20m

Chicago Midway

Sat 2/21

6:15 pm-8:30 pm

Nonstop1h 15m

$143

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Mon 2/23

1:07 pm-7:47 pm

1 stop7h 40m

Chicago Midway

Thu 2/26

3:00 pm-12:59 am

1 stop8h 59m

$150

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 2/14

6:40 am-7:05 am

Nonstop1h 25m

Chicago Midway

Sat 2/21

5:15 am-12:20 pm

1 stop6h 05m

$153

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 1/31

6:30 am-6:55 am

Nonstop1h 25m

Chicago Midway

Mon 2/2

7:55 pm-10:10 pm

Nonstop1h 15m

$157

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 2/19

1:07 pm-10:37 pm

1 stop10h 30m

Chicago Midway

Mon 2/23

9:22 pm-2:10 pm

1 stop15h 48m

$159

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 2/14

6:40 am-7:05 am

Nonstop1h 25m

Chicago Midway

Sat 2/21

6:50 am-4:15 pm

2 stops8h 25m

$159

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 1/31

6:30 am-6:55 am

Nonstop1h 25m

Chicago Midway

Mon 2/2

5:15 pm-10:45 pm

1 stop4h 30m

$167

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Sat 2/14

4:25 pm-9:50 pm

1 stop6h 25m

Chicago Midway

Sat 2/21

2:10 pm-9:35 pm

2 stops6h 25m

$168

Fort WayneChicago

FWA - MDW

FWAMDW

Fort Wayne

Sat 2/7

8:12 am-12:46 pm

1 stop5h 34m

Chicago Midway

Tue 2/10

9:33 am-1:29 pm

1 stop2h 56m

$199

Fort WayneChicago

FWA - MDW

FWAMDW

Fort Wayne

Sat 1/31

7:00 am-11:05 am

1 stop5h 05m

Chicago Midway

Sun 2/1

9:33 am-1:29 pm

1 stop2h 56m

$200

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 Indiana 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 Indiana. 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 Indiana because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $416.

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

Flying to Chicago Midway Airport from Indiana in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $353 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $413. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Indiana to Chicago Midway flight route?

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

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

There is only 1 cabin class available to choose from on Indiana 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 Indiana to Chicago Midway Airport flights?

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

Cheap Indiana to Chicago Midway Airport flight deals and tips

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

Best Price Found

$225

Fastest flight time

0h 55m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Indiana in the past 72 hours is $225. The best round-trip flight deal from Indiana to Chicago Midway Airport found on momondo in the last 72 hours is $369.
The fastest flight from Indiana to Chicago Midway Airport takes 0h 55m
Direct flights go from Indiana to Chicago Midway Airport every day.
Search flight deals

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Indiana to Chicago Midway Airport.

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

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Indiana 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
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 Indiana to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Indiana to Chicago. momondo saves you time and could save you money on your trip.

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

Yes. momondo allows you to filter the results for Indiana to Chicago flights to just show those with flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Chicago from Indiana. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Yes. momondo can track prices for Indiana to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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