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Cheap flights from Indiana to Chicago from $49

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 12/25. 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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Southwest Logo
6:45 am - 7:00 amSDF-MDW
1h 15mnonstop
Southwest Logo
8:50 pm - 11:05 pmMDW-SDF
1h 15mnonstop
$117Southwest
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Wed, Dec 3 - Tue, Dec 9
Southwest Logo
5:30 am - 10:10 amSDF-MDW
5h 40m1 stop
Southwest Logo
8:50 pm - 11:05 pmMDW-SDF
1h 15mnonstop
$127Southwest
Find Deal
Wed, Dec 3 - Tue, Dec 9
Southwest Logo
11:45 am - 8:45 pmSDF-MDW
10h 00m2 stops
Southwest Logo
10:05 am - 12:30 pmMDW-SDF
1h 25mnonstop
$132Southwest
Find Deal
Wed, Dec 3 - Tue, Dec 9
Southwest Logo
6:45 am - 7:00 amSDF-MDW
1h 15mnonstop
Southwest Logo
9:30 am - 11:45 amMDW-SDF
1h 15mnonstop
$134Southwest
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Thu, Jan 1 - Mon, Jan 5
Delta Logo
2:15 pm - 6:31 pmSDF-MDW
5h 16m1 stop
Delta Logo
9:30 am - 1:38 pmMDW-SDF
3h 08m1 stop
$157Delta
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Tue, Apr 14 - Wed, Apr 15
Delta Logo
6:00 am - 12:34 pmSDF-MDW
7h 34m2 stops
Delta Logo
5:29 pm - 11:59 pmMDW-SDF
5h 30m1 stop
$162Delta
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Wed, Dec 3 - Tue, Dec 9
Frontier Logo
7:19 pm - 10:39 pmIND-MDW
28h 20m2 stops
Frontier Logo
6:15 am - 6:50 pmMDW-IND
11h 35m1 stop
$175Frontier
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Thu, Dec 4 - Mon, Dec 8
Frontier Logo
7:14 pm - 11:25 pmCVG-MDW
5h 11m1 stop
Frontier Logo
12:25 pm - 5:48 pmMDW-CVG
28h 23m2 stops
$179Frontier
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Fri, Jan 9 - Tue, Jan 13
Multiple Airlines Logo
7:45 pm - 8:46 amIND-MDW
14h 01m1 stop
Multiple Airlines Logo
2:49 pm - 7:43 amMDW-IND
15h 54m2 stops
$199Multiple Airlines
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Mon, Dec 8 - Wed, Dec 10
Multiple Airlines Logo
5:00 am - 1:01 pmIND-MDW
9h 01m1 stop
Multiple Airlines Logo
12:18 pm - 7:53 pmMDW-IND
6h 35m1 stop
$202Multiple Airlines
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Tue, Dec 2 - Fri, Dec 5

Southwest flights from Indiana to Chicago Midway Airport

Our best Southwest deals on Indiana to Chicago Midway Airport flight tickets
Southwest
Dec 3
SDF6:45 amLouisville Intl
1h 15m
MDW7:00 amChicago Midway
Dec 9
MDW8:50 pmChicago Midway
1h 15m
SDF11:05 pmLouisville Intl
$117
Find similar
Southwest
Dec 3
SDF5:30 amLouisville Intl
5h 40m
1 stop
MDW10:10 amChicago Midway
Dec 9
MDW8:50 pmChicago Midway
1h 15m
SDF11:05 pmLouisville Intl
$127
Find similar
Southwest
Dec 3
SDF11:45 amLouisville Intl
10h 00m
2 stops
MDW8:45 pmChicago Midway
Dec 9
MDW10:05 amChicago Midway
1h 25m
SDF12:30 pmLouisville Intl
$132
Find similar

Delta flights from Indiana to Chicago Midway Airport

Our best Delta deals on Indiana to Chicago Midway Airport flight tickets
Delta
Apr 14
SDF2:15 pmLouisville Intl
5h 16m
1 stop
MDW6:31 pmChicago Midway
Apr 15
MDW9:30 amChicago Midway
3h 08m
1 stop
SDF1:38 pmLouisville Intl
$157
Find similar
Delta
Dec 3
SDF6:00 amLouisville Intl
7h 34m
2 stops
MDW12:34 pmChicago Midway
Dec 9
MDW5:29 pmChicago Midway
5h 30m
1 stop
SDF11:59 pmLouisville Intl
$162
Find similar
Delta
Jan 1
SDF6:40 amLouisville Intl
5h 26m
1 stop
MDW11:06 amChicago Midway
Jan 5
MDW5:31 pmChicago Midway
5h 24m
1 stop
SDF11:55 pmLouisville Intl
$174
Find similar

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 November 10, 2025.
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

Wed 12/3

6:45 am-7:00 am

Nonstop1h 15m

Chicago Midway

Tue 12/9

8:50 pm-11:05 pm

Nonstop1h 15m

$117

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 12/3

5:30 am-10:10 am

1 stop5h 40m

Chicago Midway

Tue 12/9

8:50 pm-11:05 pm

Nonstop1h 15m

$127

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 12/3

11:45 am-8:45 pm

2 stops10h 00m

Chicago Midway

Tue 12/9

10:05 am-12:30 pm

Nonstop1h 25m

$132

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 1/1

6:45 am-7:00 am

Nonstop1h 15m

Chicago Midway

Mon 1/5

9:30 am-11:45 am

Nonstop1h 15m

$134

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 4/14

2:15 pm-6:31 pm

1 stop5h 16m

Chicago Midway

Wed 4/15

9:30 am-1:38 pm

1 stop3h 08m

$157

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 12/3

6:00 am-12:34 pm

2 stops7h 34m

Chicago Midway

Tue 12/9

5:29 pm-11:59 pm

1 stop5h 30m

$162

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Thu 12/4

7:19 pm-10:39 pm

2 stops28h 20m

Chicago Midway

Mon 12/8

6:15 am-6:50 pm

1 stop11h 35m

$175

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Fri 1/9

7:14 pm-11:25 pm

1 stop5h 11m

Chicago Midway

Tue 1/13

12:25 pm-5:48 pm

2 stops28h 23m

$179

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Mon 12/8

7:45 pm-8:46 am

1 stop14h 01m

Chicago Midway

Wed 12/10

2:49 pm-7:43 am

2 stops15h 54m

$199

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Tue 12/2

5:00 am-1:01 pm

1 stop9h 01m

Chicago Midway

Fri 12/5

12:18 pm-7:53 pm

1 stop6h 35m

$202

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, Wednesday is the cheapest day to fly to Chicago Midway Airport from Indiana. The lowest ticket price found for a Wednesday departure recently was $297. 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 $386.

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 $317 when looking at flights departing in the afternoon. Try not to purchase tickets in the evening because they tend to be around $380. 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?

You could potentially save up to 13% on your flight if you consider stops on a Indiana to Chicago Midway Airport flight.

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

$161

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 $161. The best round-trip flight deal from Indiana to Chicago Midway Airport found on momondo in the last 72 hours is $297.
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
Crown Point
Munster
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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