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$67+ 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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
IND — CHI
Jun 6 — Jun 131
Sat 6/6
Sat 6/13
1 adult, Economy
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Cheap 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 May 7, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1212:20 pm
IND
-
ORD
1 stop8h 33m
Frontier
Tue 8/181:50 pm
ORD
-
IND
1 stop20h 29m
Frontier
Deal found 5/5$131
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2712:14 pm
IND
-
ORD
1 stop20h 41m
Frontier
Tue 6/26:55 am
ORD
-
IND
1 stop27h 28m
Frontier
Deal found 5/3$145
This United Airlines deal was found by Cheapflights users on 5/3. 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 6/28:08 pm
IND
-
ORD
Nonstop1h 27m
United Airlines
Tue 6/912:58 pm
ORD
-
IND
Nonstop1h 16m
United Airlines
Deal found 5/3$157
This Southwest deal was found by Cheapflights users on 5/4. 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.
Wed 6/35:10 pm
IND
-
MDW
Nonstop1h 00m
Southwest
Wed 6/109:20 pm
MDW
-
IND
Nonstop1h 05m
Southwest
Deal found 5/4$157
This American Airlines deal was found by Cheapflights users on 5/2. 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 6/1612:20 pm
IND
-
ORD
Nonstop1h 28m
American Airlines
Tue 6/231:14 pm
ORD
-
IND
Nonstop1h 12m
American Airlines
Deal found 5/2$159
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:14 pm
IND
-
ORD
1 stop20h 49m
Frontier
Tue 7/211:50 pm
ORD
-
IND
1 stop20h 15m
Frontier
Deal found 5/3$168
This Southwest deal was found by Cheapflights users on 5/3. 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 6/166:40 am
IND
-
MDW
Nonstop1h 10m
Southwest
Tue 6/237:50 am
MDW
-
IND
2 stops7h 25m
Southwest
Deal found 5/3$172
This Delta deal was found by Cheapflights users on 5/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/24:49 pm
IND
-
ORD
1 stop5h 31m
Delta
Tue 6/93:55 pm
ORD
-
IND
1 stop7h 22m
Delta
Deal found 5/3$177
This American Airlines deal was found by Cheapflights users on 5/4. 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.
Wed 6/310:37 am
IND
-
ORD
Nonstop1h 23m
American Airlines
Thu 6/48:41 pm
ORD
-
IND
Nonstop1h 24m
American Airlines
Deal found 5/4$189
This Southwest deal was found by Cheapflights users on 5/2. 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 5/232:40 pm
IND
-
MDW
Nonstop1h 00m
Southwest
Tue 6/210:00 am
MDW
-
IND
Nonstop1h 05m
Southwest
Deal found 5/2$189
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/612:20 pm
IND
-
ORD
1 stop20h 33m
Frontier
Tue 8/117:05 am
ORD
-
IND
1 stop27h 00m
Frontier
Deal found 5/3$192
This Southwest deal was found by Cheapflights users on 5/5. 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 6/26:40 am
IND
-
MDW
Nonstop0h 55m
Southwest
Tue 6/911:25 am
MDW
-
IND
2 stops9h 30m
Southwest
Deal found 5/5$192

Find flight deals from Indiana to Chicago

Keep the following information in mind while searching for Indiana to Chicago flight deals. Data was last updated May 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$131
(Kiwi.com)

One-way from

$67
(Kiwi.com)

Popular in

March

Cheapest in

August

Average price

$236

Good round-trip deal

$339 or less

Good one-way deal

$193 or less
Provider with most accurate pricing for Indianapolis-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Indianapolis-Chicago (CHI) flights.
Search Deals
From Indiana to Chicago (CHI)
Search Deals
One-way flight from Indiana to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Indiana to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Indiana to Chicago (CHI).
Search Deals

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 May 7, 2026.
Use the filters below to find and compare flights from Indiana to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

IndianapolisChicago

IND - ORD

INDORD

Indianapolis

Tue 6/2

4:49 pm-9:20 pm

1 stop5h 31m

Chicago O'Hare Intl

Tue 6/9

3:55 pm-12:17 am

1 stop7h 22m

$177

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Tue 6/2

5:50 am-10:40 am

1 stop5h 50m

Chicago Midway

Tue 6/9

9:20 pm-11:25 pm

Nonstop1h 05m

$187

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Sat 5/23

2:40 pm-2:40 pm

Nonstop1h 00m

Chicago Midway

Tue 6/2

10:00 am-12:05 pm

Nonstop1h 05m

$189

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 5/23

12:50 pm-5:10 pm

2 stops5h 20m

Chicago Midway

Thu 5/28

1:00 pm-3:10 pm

Nonstop1h 10m

$206

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Sat 6/6

1:40 pm-7:15 pm

2 stops6h 35m

Chicago Midway

Mon 6/8

7:05 pm-9:15 pm

Nonstop1h 10m

$206

CincinnatiChicago

CVG - ORD

CVGORD

Cincinnati Cinci./N. Kentucky

Thu 5/28

6:00 pm-9:53 pm

1 stop4h 53m

Chicago O'Hare Intl

Mon 6/1

7:00 am-1:27 pm

1 stop5h 27m

$211

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Wed 6/10

7:40 pm-7:50 pm

Nonstop1h 10m

Chicago Midway

Sat 6/13

12:50 pm-3:00 pm

Nonstop1h 10m

$215

CincinnatiChicago

CVG - MDW

CVGMDW

Cincinnati Cinci./N. Kentucky

Thu 5/28

5:45 am-1:10 pm

2 stops8h 25m

Chicago Midway

Mon 6/1

5:30 am-11:50 am

1 stop5h 20m

$216

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Thu 10/1

6:55 am-6:55 am

Nonstop1h 00m

Chicago Midway

Mon 10/5

9:55 am-12:00 pm

Nonstop1h 05m

$221

IndianapolisChicago

IND - MDW

INDMDW

Indianapolis

Thu 5/28

6:50 am-6:45 am

Nonstop0h 55m

Chicago Midway

Mon 6/1

9:45 pm-11:55 pm

Nonstop1h 10m

$221

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/2

Showing 1-10 of 60 resultsSorted by cheapest first
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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

How far ahead should I book a flight from Indiana to Chicago?

Booking 82 days in advance of your planned departure date is, on average, the best time to get cheap flights from Indiana to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 $98). Flying from Indiana to Chicago in November is currently the most expensive (average of $179). 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 May 7, 2026.

It’s typically best to fly out from Indiana to Chicago in the morning. Doing so could potentially save you 32% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from Indiana to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Indiana to Chicago. Price data was last updated on May 2, 2026.

Travelers seeking maximum savings on their Indiana to Chicago flight should consider departing on Tuesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 May 7, 2026.

The most flights from USIN to CHI are scheduled on a Monday (98 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (65 on average).

How much does it cost to fly round-trip from Indiana to Chicago?

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 $239, Delta can have you in Chicago from Indiana in 1h 20m. There are 156 mi between Indiana and Chicago. This flight may include one or multiple stops.

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

    The cheapest airline one-way is Southern / Mokulele, with whom users have recently found tickets for as low as $93. However, be on the lookout for offers from United Airlines and American Airlines, 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 Louisville Intl - Chicago O'Hare Intl 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 GoJet (100%), Finnair (80%) and Republic Airways (79%).

  • What are the cheapest flights from Indiana to Chicago?

    Looking at all options, your cheapest flight can be booked for $146. While the most popular route (Cincinnati Cinci./N. Kentucky - Chicago O'Hare Intl) can be booked for $175 on average, our data indicates $1,035 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 $98). Flying from Indiana to Chicago in November is currently the most expensive (average of $179). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 May 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$136Average$309FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$157Average$248FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$192Average$337FlexibilityNo cancel feeOn-time63%

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