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$49+ Cheap flights from Indiana to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
IND — CHI
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Indiana to Chicago

Keep the following information in mind while searching for Indiana to Chicago flight deals. Data was last updated September 15, 2025.

Round-trip from

$107
(Southwest)

One-way from

$49
(United Airlines)

Popular in

March

Cheapest in

August

Average price

$257

Good round-trip deal

$260 or less

Good one-way deal

$140 or less
From Indiana to Chicago (CHI)
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One-way flight from Indiana to Chicago (CHI)
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Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Indiana to Chicago (CHI).
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Price to beat on a one-way flight from Indiana to Chicago (CHI).
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Find flight deals from Indiana to Chicago

Cheapest flights from Indiana to Chicago
Explore the most affordable flight options available from Indiana to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/43:20 pmSDF - MDW
1 stop6h 45mSouthwest
Thu 11/67:15 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 9/15$107
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1411:55 amSDF - MDW
Nonstop1h 15mSouthwest
Tue 10/2112:30 pmMDW - SDF
1 stop8h 10mSouthwest
Deal found 9/14$113
This American Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/77:25 pmIND - ORD
Nonstop1h 19mAmerican Airlines
Thu 10/94:38 pmORD - IND
Nonstop1h 05mAmerican Airlines
Deal found 9/12$115
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/87:00 amSDF - ORD
Nonstop1h 40mUnited Airlines
Sun 11/96:10 pmORD - SDF
Nonstop1h 34mUnited Airlines
Deal found 9/12$115
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/81:10 pmSDF - MDW
1 stop6h 55mSouthwest
Wed 11/128:25 amMDW - SDF
2 stops7h 45mSouthwest
Deal found 9/15$122
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/37:15 amIND - ORD
Nonstop1h 17mUnited Airlines
Sun 10/59:03 amORD - IND
Nonstop1h 14mUnited Airlines
Deal found 9/12$131
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/146:45 amSDF - ORD
Nonstop1h 33mAmerican Airlines
Fri 10/178:21 pmORD - SDF
Nonstop1h 35mAmerican Airlines
Deal found 9/15$134
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/208:15 pmSDF - MDW
Nonstop1h 15mSouthwest
Fri 10/249:25 pmMDW - SDF
Nonstop1h 15mSouthwest
Deal found 9/14$134
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/84:20 pmIND - ORD
1 stop8h 52mFrontier
Mon 11/105:05 amORD - IND
1 stop5h 17mFrontier
Deal found 9/14$144
This Frontier deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/259:34 pmIND - ORD
1 stop10h 40mFrontier
Sat 11/18:00 amORD - IND
1 stop11h 41mFrontier
Deal found 9/13$145
This Frontier deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1711:31 amIND - ORD
1 stop7h 26mFrontier
Mon 10/205:25 amORD - IND
1 stop7h 26mFrontier
Deal found 9/13$148
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/49:00 amSDF - ORD
Nonstop1h 40mUnited Airlines
Thu 11/67:30 amORD - SDF
Nonstop1h 29mUnited Airlines
Deal found 9/14$152

Cheapflights Fare Finder

 
Customize your flight search to find flights from Indiana to Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Indiana to Chicago that are best for you.

Fly from

Indiana

Fly to

Chicago

Route

Depart

Return

Price

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Thu 12/4

6:45 am-7:00 am

Nonstop1h 15m

Chicago Midway

Wed 1/7

8:10 am-4:50 pm

2 stops7h 40m

$112

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Tue 10/7

7:25 pm-7:44 pm

Nonstop1h 19m

Chicago O'Hare Intl

Thu 10/9

4:38 pm-6:43 pm

Nonstop1h 05m

$115

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Sat 11/8

7:00 am-7:40 am

Nonstop1h 40m

Chicago O'Hare Intl

Sun 11/9

6:10 pm-8:44 pm

Nonstop1h 34m

$115

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 12/10

11:45 am-8:30 pm

2 stops9h 45m

Chicago Midway

Mon 1/12

5:15 pm-10:45 pm

1 stop4h 30m

$122

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Fri 10/3

7:15 am-7:32 am

Nonstop1h 17m

Chicago O'Hare Intl

Sun 10/5

9:03 am-11:17 am

Nonstop1h 14m

$131

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Sat 11/8

4:20 pm-12:12 am

1 stop8h 52m

Chicago O'Hare Intl

Mon 11/10

5:05 am-11:22 am

1 stop5h 17m

$144

LouisvilleChicago

SDF - MDW

SDFMDW

Louisville Intl

Wed 10/22

1:45 pm-7:05 pm

1 stop6h 20m

Chicago Midway

Fri 10/24

9:25 pm-11:40 pm

Nonstop1h 15m

$144

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Mon 10/13

8:45 am-9:23 am

Nonstop1h 38m

Chicago O'Hare Intl

Mon 10/20

7:50 pm-10:30 pm

Nonstop1h 40m

$157

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Fri 10/17

11:31 am-5:57 pm

1 stop7h 26m

Chicago O'Hare Intl

Sun 10/19

5:25 am-1:51 pm

1 stop7h 26m

$161

LouisvilleChicago

SDF - ORD

SDFORD

Louisville Intl

Tue 11/11

6:15 am-12:28 pm

1 stop7h 13m

Chicago O'Hare Intl

Tue 11/11

8:25 pm-10:55 pm

Nonstop1h 30m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 60 results
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Best time to book a flight from Indiana to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Indiana with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Indiana to Chicago

What is the cheapest month to book a flight from Indiana to Chicago?

Currently, August is the cheapest month in which you can book a flight from Indiana to Chicago (average of $245). Flying from Indiana to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from IN to CHI?

Find hourly flight availability from Indiana to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

When flying from Indiana to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Indiana to Chicago

Explore weekly flight availability from Indiana to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 15, 2025.

The most flights from USIN to CHI are scheduled on a Monday (74 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (55 on average).

Related info for your journey

Find useful and relevant information for your journey from Indiana to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Indiana to Chicago?

    For as low as $112, Southwest can have you in Chicago from Indiana in 1h 15m. There are 271 mi between Indiana and Chicago. All flights are typically nonstop.

  • What are the cheapest airlines to fly from Indiana to Chicago one-way?

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $49. However, be on the lookout for offers from Southwest and Frontier, as they are both options that can get you from Indiana to Chicago for a low price.

  • What are the most popular routes from Indiana to Chicago?

    While some choose either Cincinnati Cinci./N. Kentucky - Chicago Midway or Indianapolis - Chicago O'Hare Intl, Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl is the most popular route from Indiana to Chicago.

  • What are the most reliable airlines from Indiana to Chicago?

    The top 3 most reliable airlines when flying from Indiana to Chicago are Finnair (90%), Envoy Air (89%) and Copa Airlines (86%).

  • What are the cheapest flights from Indiana to Chicago?

    Looking at all options, your cheapest flight can be booked for $111. While the most popular route (Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl) can be booked for $184 on average, our data indicates $882 when flying from Indiana to Chicago.

  • Can I find deals for flights from Indiana to Chicago that include hotel bookings?

    Yes. In addition to deals on Indiana to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Indiana to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Indiana to Chicago.

  • Can I find deals for business class flights from Indiana to Chicago?

    Yes. Cheapflights offers flight deals from Indiana to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Indiana to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Indiana to Chicago (average of $245). Flying from Indiana to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Indiana to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Indiana to Chicago

Discover the top 3 airlines that operate flights from Indiana to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$148Average$314FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$160Average$256FlexibilityNo cancel feeOn-time69%
Southern / MokuleleCheapest$189Average$302FlexibilityNo cancel feeOn-timeN/A

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