Can I fly direct from Indianapolis to Chicago?

Yes, direct flights from Indianapolis to Chicago are available. Historically, approximately 46.3% of flights on this route have been direct. For flights that include stopovers, travelers typically experience a median of 2 stopovers across the trailing 90 days.

How long is the flight from Indianapolis to Chicago?

The median direct flight time from Indianapolis to Chicago is typically 1 hour and 22 minutes. This route covers an approximate distance of 261 kilometers. Flights with one stopover, however, have a significantly longer median duration, averaging 10 hours and 57 minutes.

How often do cheap flights from Indianapolis to Chicago come up?

Historically, cheap flights from Indianapolis to Chicago come up frequently. This route is consistently identified as one with regular opportunities for finding lower fares. Travelers can typically expect to see favorable pricing options appear often.

Flights From Indianapolis

To Chicago

Cheap Flights from Indianapolis to Chicago

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Deals from

Indianapolis

RatePunk searches hundreds of travel sites at once for deals on flights to Chicago

Prices updated 6 days ago

406 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated Aug 2, 2026.)

Today’s best flight deals from Indianapolis to Chicago

Explore current cheapest deals departing from Indianapolis to Chicago

2026-08-20 – 2026-08-24
IND - Chicago
42% AI deal score
$147
$157
Round trip
2026-09-08 – 2026-09-15
IND - Chicago
39% AI deal score
$128
$157
Round trip
2026-09-05 – 2026-09-06
IND - Chicago
41% AI deal score
$130
$157
Round trip
2026-08-20 – 2026-08-24
IND - Chicago
39% AI deal score
$158
$157
Round trip
2026-10-17 – 2026-10-28
IND - Chicago
40% AI deal score
$111
$158
Round trip
2026-11-19 – 2026-11-26
IND - Chicago
40% AI deal score
$141
$158
Round trip
2026-12-10 – 2026-12-17
IND - Chicago
42% AI deal score
$165
$158
Round trip
2026-12-07 – 2026-12-14
IND - Chicago
42% AI deal score
$165
$158
Round trip
2026-12-09 – 2026-12-16
IND - Chicago
44% AI deal score
$167
$158
Round trip
2026-12-02 – 2026-12-09
IND - Chicago
42% AI deal score
$165
$158
Round trip

Indianapolis to Chicago: Overview

Insights for flights from Indianapolis to Chicago

A typical journey from Indianapolis to Chicago takes about 2h 46m, including connections. Given that a meaningful share of itineraries on this route include layovers, this duration accounts for the time spent on connecting flights. Travelers should factor in this total journey time when planning their trip.

For those looking for cheap flights from Indianapolis to Chicago, prices typically range from $226–$535, with a median of $312. Right now, current fares are significantly above the typical level, and only 1% of recent fares were classified as a good price. New deals appear almost daily, so setting up a price alert can help you find better value.

When is the cheapest time to fly from Indianapolis to Chicago? Historically, the most affordable months to fly are April, with a median fare of $219, and October and December, both with median fares of $227. These months offer the best opportunities for finding lower prices compared to the overall median.

A meaningful share of recent fares, specifically 46.3%, are for direct flights from Indianapolis to Chicago. For the remaining itineraries that include connections, travelers can expect a median of 2 stopovers. This mix means you have options for both non-stop travel and itineraries with layovers, depending on your preference for convenience versus potential cost savings.

The distance between Indianapolis and Chicago is 261 kilometers, classifying this as a short-haul route. This means you can expect a relatively quick journey, making it suitable for short trips or weekend getaways.

How much is a round trip from Indianapolis to Chicago

Regular price: $109 - $238

Prices for flights from Indianapolis to Chicago are currently within the regular range.

The regular price range for this route is $109 to $238. The current lowest deal is $157 with American Airlines for travel from Aug 20-Aug 24.

now $157

Low $109

High $238

The cheapest time to fly from Indianapolis to Chicago

The cheapest month to fly from Indianapolis to Chicago is April, with a median price of $219. The most expensive month is February, with a median price of $952. Prices are generally lower from January to December.

April

Cheapest

Flights from $219

February

Most Expensive

Flights from $952

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Indianapolis to Chicago

American Airlines

Southwest Airlines

Last-minute flights going from Indianapolis to Chicago

Tue, Aug 4

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (MDW)

Deutsche Luft Hansa

$421

$434

One-way

Tue, Aug 4

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (MDW)

$517

$491

One-way

Tue, Aug 4

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (MDW)

$536

$535

One-way

Wed, Aug 5

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (ORD)

Frontier Airlines

$478

$341

One-way

Fri, Aug 7

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (ORD)

Frontier Airlines

$437

$361

One-way

Wed, Aug 12

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (ORD)

Frontier Airlines

$310

$276

One-way

Biggest price drops on these dates for flights from Indianapolis to Chicago

2 nights

Aug 13 - Aug 15

$296 → $177

40%

14 nights

Dec 17 - Dec 31

$268 → $157

41%

3 nights

Aug 19 - Aug 22

$283 → $177

37%

1 night

Aug 24 - Aug 25

$283 → $177

38%

Popular Airports to fly from Indianapolis to Chicago

Indianapolis - Chicago route insights

💸 Price insights

Recent fares are above the typical level.

Recent fares from Indianapolis to Chicago are above the typical level at $157.

📅 Best time to fly

April is historically the cheapest month to fly.

Historically, April is the cheapest month to fly from Indianapolis to Chicago, with a median price of $219.

⏱️ Flight duration

Flights are typically 2h 46m long.

Flights from Indianapolis to Chicago typically take 2h 46m, covering a distance of 261 km.

✈️ Airlines & availability

46.3% of recent flights are direct.

46.3% of recent flights from Indianapolis to Chicago are direct, with frequent deals available.

🏆 Airline highlight

American Airlines offers a recent deal for $157.

American Airlines has a recent deal from Indianapolis to Chicago for $157, departing August 20.

🎯 Booking tip

Consider booking in April for lower prices.

Historically, April offers lower median prices for flights from Indianapolis to Chicago.

Indianapolis main airports to depart from

Indianapolis International (IND)

Cheapest

Indianapolis International is a convenient departure airport for flights from Indianapolis to Chicago.

📍 ~15 km from city center (reachable by car)

💸 Flights from ~$157

Chicago main airports to arrive at

Chicago Midway International (MDW)

Cheapest

Chicago Midway International is a convenient arrival airport for flights from Indianapolis to Chicago.

📍 ~15 km from city center (reachable by car)

💸 Flights from ~$157

Airports nearby Chicago used as alternative

General Mitchell International (MKE)

General Mitchell International offers significant carrier presence and direct flight options for Chicago travelers.

📍 ~135 km from Chicago (reachable by train or car)

💸 Flights from ~$248

Business & First Class Flight Deals to Chicago

65% AI deal score

$540

$437

Save $103

Frequently Asked Questions About Flights to Chicago

Historically, the optimal booking window for flights from Indianapolis to Chicago is typically 14-27 days prior to departure. Flights booked within this period have an average price of $209. Booking 7-13 days out sees an average price of $328, while waiting until 0-6 days before departure can result in an average price of $405. Conversely, booking more than 60 days in advance tends to be more expensive, with an average price of $447.

Across the trailing quarter, a good price for a flight from Indianapolis to Chicago is considered to be $226 or less. The median price for this route during the same period was $312. Prices can vary, with 75% of observed fares being $535 or less.

Historically, April, October, and December have offered the cheapest flights from Indianapolis to Chicago. In April, the median price was $219, while October and December both had a median price of $227. These prices are notably lower than the annual median price of $312 for this route.

Related routes

More routes from Indianapolis

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Flights to Chicago from other cities

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Indianapolis to Chicago: Overview

Insights for flights from Indianapolis to Chicago

How much is a round trip from Indianapolis to Chicago

Regular price: $109 - $238

Prices for flights from Indianapolis to Chicago are currently within the regular range.

The regular price range for this route is $109 to $238. The current lowest deal is $157 with American Airlines for travel from Aug 20-Aug 24.

now $157

Low $109

High $238

The cheapest time to fly from Indianapolis to Chicago

April

Cheapest

Flights from $219

February

Most Expensive

Flights from $952

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Indianapolis to Chicago

American Airlines

Southwest Airlines

Last-minute flights going from Indianapolis to Chicago

Tue, Aug 4

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (MDW)

Deutsche Luft Hansa

$421

$434

One-way

Tue, Aug 4

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (MDW)

$517

$491

One-way

Tue, Aug 4

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (MDW)

$536

$535

One-way

Wed, Aug 5

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (ORD)

Frontier Airlines

$478

$341

One-way

Fri, Aug 7

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (ORD)

Frontier Airlines

$437

$361

One-way

Wed, Aug 12

⌛ Last-Minute

IND - Chicago

Indianapolis (IND) - Chicago (ORD)

Frontier Airlines

$310

$276

One-way

Biggest price drops on these dates for flights from Indianapolis to Chicago

2 nights

Aug 13 - Aug 15

$296 → $177

40%

14 nights

Dec 17 - Dec 31

$268 → $157

41%

3 nights

Aug 19 - Aug 22

$283 → $177

37%

1 night

Aug 24 - Aug 25

$283 → $177

38%

Popular Airports to fly from Indianapolis to Chicago