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Cheap flights from Indiana to Chicago from $53

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 9/9. 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
4:00 pm - 4:20 pmSDF-MDW
1h 20mnonstop
Southwest Logo
8:35 pm - 10:50 pmMDW-SDF
1h 15mnonstop
$111Southwest
Find Deal
Sat, Sep 6 - Mon, Sep 8
Southwest Logo
6:25 am - 6:40 amSDF-MDW
1h 15mnonstop
Southwest Logo
8:35 pm - 10:50 pmMDW-SDF
1h 15mnonstop
$117Southwest
Find Deal
Thu, Sep 4 - Mon, Sep 8
Southwest Logo
8:15 pm - 8:30 pmSDF-MDW
1h 15mnonstop
Southwest Logo
3:20 pm - 5:30 pmMDW-SDF
1h 10mnonstop
$122Southwest
Find Deal
Fri, Oct 10 - Tue, Oct 14
Southwest Logo
4:20 pm - 7:50 pmSDF-MDW
4h 30m1 stop
Southwest Logo
10:00 am - 12:20 pmMDW-SDF
1h 20mnonstop
$127Southwest
Find Deal
Thu, Sep 11 - Mon, Sep 15
Frontier Logo
5:44 pm - 11:17 pmCVG-MDW
6h 33m1 stop
Frontier Logo
9:00 am - 2:23 pmMDW-CVG
4h 23m1 stop
$172Frontier
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Sat, Sep 20 - Wed, Sep 24
Delta Logo
12:31 pm - 5:35 pmSDF-MDW
6h 04m1 stop
Delta Logo
10:35 am - 6:36 pmMDW-SDF
7h 01m1 stop
$177Delta
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Tue, Sep 23 - Wed, Sep 24
Delta Logo
6:00 am - 12:28 pmSDF-MDW
7h 28m2 stops
Delta Logo
6:00 am - 11:43 amMDW-SDF
4h 43m1 stop
$182Delta
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Tue, Sep 23 - Wed, Sep 24
Frontier Logo
5:59 pm - 11:08 pmCVG-MDW
6h 09m1 stop
Frontier Logo
6:15 am - 4:32 pmMDW-CVG
9h 17m1 stop
$188Frontier
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Thu, Aug 21 - Mon, Aug 25
Logo
7:45 am - 4:20 pmSDF-MDW
9h 35m1 stop
Logo
11:31 am - 10:57 pmMDW-SDF
10h 26m1 stop
$233
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Fri, Oct 17 - Sat, Oct 25
Logo
7:45 am - 4:20 pmSDF-MDW
9h 35m1 stop
Logo
9:45 am - 8:26 pmMDW-SDF
9h 41m2 stops
$255
Find Deal
Fri, Oct 17 - Mon, Oct 20

Delta flights from Indiana to Chicago Midway Airport

Our best Delta deals on Indiana to Chicago Midway Airport flight tickets
Delta
Sep 23
SDF12:31 pmLouisville Intl
6h 04m
1 stop
MDW5:35 pmChicago Midway
Sep 24
MDW10:35 amChicago Midway
7h 01m
1 stop
SDF6:36 pmLouisville Intl
$177
Find similar
Delta
Sep 23
SDF6:00 amLouisville Intl
7h 28m
2 stops
MDW12:28 pmChicago Midway
Sep 24
MDW6:00 amChicago Midway
4h 43m
1 stop
SDF11:43 amLouisville Intl
$182
Find similar
Delta
Sep 13
SDF10:32 amLouisville Intl
9h 03m
2 stops
MDW6:35 pmChicago Midway
Sep 16
MDW1:08 pmChicago Midway
9h 44m
2 stops
SDF11:52 pmLouisville Intl
$187
Find similar

Southwest flights from Indiana to Chicago Midway Airport

Our best Southwest deals on Indiana to Chicago Midway Airport flight tickets
Southwest
Sep 6
SDF4:00 pmLouisville Intl
1h 20m
MDW4:20 pmChicago Midway
Sep 8
MDW8:35 pmChicago Midway
1h 15m
SDF10:50 pmLouisville Intl
$111
Find similar
Southwest
Sep 4
SDF6:25 amLouisville Intl
1h 15m
MDW6:40 amChicago Midway
Sep 8
MDW8:35 pmChicago Midway
1h 15m
SDF10:50 pmLouisville Intl
$117
Find similar
Southwest
Oct 10
SDF8:15 pmLouisville Intl
1h 15m
MDW8:30 pmChicago Midway
Oct 14
MDW3:20 pmChicago Midway
1h 10m
SDF5:30 pmLouisville Intl
$122
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 August 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

Sat 9/6

4:00 pm-4:20 pm

Nonstop1h 20m

Chicago Midway

Mon 9/8

8:35 pm-10:50 pm

Nonstop1h 15m

$111

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 9/4

6:25 am-6:40 am

Nonstop1h 15m

Chicago Midway

Mon 9/8

8:35 pm-10:50 pm

Nonstop1h 15m

$117

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Fri 10/10

8:15 pm-8:30 pm

Nonstop1h 15m

Chicago Midway

Tue 10/14

3:20 pm-5:30 pm

Nonstop1h 10m

$122

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 9/11

4:20 pm-7:50 pm

1 stop4h 30m

Chicago Midway

Mon 9/15

10:00 am-12:20 pm

Nonstop1h 20m

$127

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 9/20

5:44 pm-11:17 pm

1 stop6h 33m

Chicago Midway

Wed 9/24

9:00 am-2:23 pm

1 stop4h 23m

$172

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 9/23

12:31 pm-5:35 pm

1 stop6h 04m

Chicago Midway

Wed 9/24

10:35 am-6:36 pm

1 stop7h 01m

$177

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Tue 9/23

6:00 am-12:28 pm

2 stops7h 28m

Chicago Midway

Wed 9/24

6:00 am-11:43 am

1 stop4h 43m

$182

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 8/21

5:59 pm-11:08 pm

1 stop6h 09m

Chicago Midway

Mon 8/25

6:15 am-4:32 pm

1 stop9h 17m

$188

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Fri 10/17

7:45 am-4:20 pm

1 stop9h 35m

Chicago Midway

Sat 10/25

11:31 am-10:57 pm

1 stop10h 26m

$233

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Fri 10/17

7:45 am-4:20 pm

1 stop9h 35m

Chicago Midway

Mon 10/20

9:45 am-8:26 pm

2 stops9h 41m

$255

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 $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 Indiana because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $357.

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 $296 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $325. 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 are 1 cabin classes 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

$53

Fastest flight time

1h 00m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Indiana in the past 72 hours is $53. The best round-trip flight deal from Indiana to Chicago Midway Airport found on momondo in the last 72 hours is $111.
The fastest flight from Indiana to Chicago Midway Airport takes 1h 00m
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
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 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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