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Flights from Indianapolis to Chicago

Search for direct flights from Indianapolis to Chicago in the next 3 months. Based on Trip.com's latest 7-day flight data, one-way direct flights start at US$80, and round-trip direct flights start at US$123.

      • Cheapest nonstop
        IND 05:55
        1h 24m
        Nonstop
        ORD 06:19
        Indianapolis - Chicago | Wed, May 20 | American Airlines
        ORD 06:54
        1h 19m
        Nonstop
        IND 09:13
        Chicago - Indianapolis | Wed, May 27 | American Airlines
        US$123 US$207
        41% off
        41% off
        US$207 US$123
      • IND 12:20
        1h 28m
        Nonstop
        ORD 12:48
        Indianapolis - Chicago | Fri, Jun 19 | American Airlines
        ORD 13:14
        1h 12m
        Nonstop
        IND 15:26
        Chicago - Indianapolis | Fri, Jun 26 | American Airlines
        US$160 US$207
        23% off
        23% off
        US$207 US$160
      • IND 10:38
        1h 22m
        Nonstop
        ORD 11:00
        Indianapolis - Chicago | Sat, Jun 27 | American Airlines
        ORD 22:30
        1h 22m
        Nonstop
        IND 00:52
        Chicago - Indianapolis | Sat, Jun 27 | American Airlines
        US$160 US$207
        23% off
        23% off
        US$207 US$160
      • IND 05:10
        1h 22m
        Nonstop
        ORD 05:32
        Indianapolis - Chicago | Sat, Jun 20 | American Airlines
        ORD 22:30
        1h 22m
        Nonstop
        IND 00:52
        Chicago - Indianapolis | Sat, Jun 27 | American Airlines
        US$161
        22% off
        US$207 US$161
      • IND 13:50
        1h 22m
        Nonstop
        ORD 14:12
        Indianapolis - Chicago | Fri, May 22 | American Airlines
        ORD 22:31
        1h 24m
        Nonstop
        IND 00:55
        Chicago - Indianapolis | Fri, May 29 | American Airlines
        US$165
        20% off
        US$207 US$165
      • IND 05:10
        1h 23m
        Nonstop
        ORD 05:33
        Indianapolis - Chicago | Fri, Jun 12 | American Airlines
        ORD 22:31
        1h 24m
        Nonstop
        IND 00:55
        Chicago - Indianapolis | Fri, Jun 12 | American Airlines
        US$166
        20% off
        US$207 US$166
      • IND 10:59
        1h 20m
        Nonstop
        ORD 11:19
        Indianapolis - Chicago | Sat, May 16 | American Airlines
        ORD 16:50
        1h 13m
        Nonstop
        IND 19:03
        Chicago - Indianapolis | Sat, May 23 | American Airlines
        US$169
        18% off
        US$207 US$169
      • IND 10:30
        3h 34m
        1 stop
        ORD 13:04
        Indianapolis - Chicago | Sat, Jun 27 | Delta Air Lines
        MDW 21:20
        1h 5m
        Nonstop
        IND 23:25
        Chicago - Indianapolis | Sat, Jun 27 |
        US$165
        20% off
        US$207 US$165
      • IND 13:00
        17h 25m
        1 stop
        CHI 14:00
        Indianapolis - Chicago | Sun, May 17 | Normal Airline
        CHI 15:00
        6h
        Nonstop
        IND 16:00
        Chicago - Indianapolis | Tue, May 19 | Normal Airline
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      • Cheapest nonstop
        IND 09:40
        1h 20m
        Nonstop
        ORD 10:00
        Indianapolis - Chicago | Sat, May 23 | American Airlines
        US$80 US$247
        68% off
        68% off
        US$247 US$80
      • IND 20:49
        1h 28m
        Nonstop
        ORD 21:17
        Indianapolis - Chicago | Fri, Jun 19 | American Airlines
        US$80 US$247
        68% off
        68% off
        US$247 US$80
      • IND 12:11
        1h 24m
        Nonstop
        ORD 12:35
        Indianapolis - Chicago | Sat, Jul 4 | American Airlines
        US$81 US$247
        67% off
        67% off
        US$247 US$81
      • IND 06:46
        1h 29m
        Nonstop
        ORD 07:15
        Indianapolis - Chicago | Fri, Jun 5 | American Airlines
        US$84
        66% off
        US$247 US$84
      • IND 09:40
        1h 20m
        Nonstop
        ORD 10:00
        Indianapolis - Chicago | Fri, May 22 | American Airlines
        US$162
        34% off
        US$247 US$162
      • IND 20:49
        1h 36m
        Nonstop
        ORD 21:25
        Indianapolis - Chicago | Fri, May 29 | American Airlines
        US$202
        18% off
        US$247 US$202
      • IND 06:30
        3h 13m
        1 stop
        MDW 08:43
        Indianapolis - Chicago | Mon, Jun 8 | Delta Air Lines
        US$77
        69% off
        US$247 US$77
      • IND 06:00
        5h 7m
        1 stop
        MDW 10:07
        Indianapolis - Chicago | Fri, Jun 19 | Delta Air Lines
        US$83
        66% off
        US$247 US$83
      • IND 13:00
        17h 25m
        1 stop
        CHI 14:00
        Indianapolis - Chicago | Sun, May 17 | Normal Airline
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        Find more flights

Displayed flight fares from Indianapolis to Chicago are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

Trip.com Price Insights on Flights from Indianapolis to Chicago

Which month has the cheapest one-way flights from to Chicago?

Average monthly one-way flight prices from to Chicago, based on bookings made by Trip.com users over the past 12 months.

Based on Trip.com’s data, the cheapest month for flights from to Chicago is June, with an average price of US$162; while the month with the highest flight price is usually January, with an average price of up to US$281.

US$281
US$222
US$162
US$103
    Cheapest
  • US$181
    May
  • US$162
    Jun
  • US$247
    Jul
  • US$177
    Aug
  • US$213
    Sep
  • US$197
    Oct
  • US$237
    Nov
  • US$187
    Dec
  • US$281
    Jan
  • US$208
    Feb
  • US$209
    Mar
  • US$224
    Apr

Frequently Asked Questions

  • What are the cheapest flights from Indianapolis to Chicago (IND-CHI)?

    Based on Trip.com data, Delta Air Lines offers one-way fares as low as US$77 on Cheapest nonstop routes (e.g. IND to MDW on Mon, Jun 8), while American Airlines offers Cheapest nonstop round-trips from US$123 departing on Wed, May 20 and returning on Wed, May 27.
  • At the moment, you can catch a nonstop flight from Indianapolis to Chicago with the following airlines, including: United Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.
  • It takes about 1 hour 22 minutes to fly from Indianapolis to Chicago.
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Indianapolis to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • Based on Trip.com data in the past 4 weeks, there is 89 flight per week flying from Indianapolis to Chicago. You can check the weekly schedule for popular airlines on this route below: United Airlines: S/M/T/W/T/F/S -- UA5238 (11:16)
  • To find best deals on flights from Indianapolis to Chicago, you can use various tools on Trip.com:
    · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Mon, Jun 8, with one-way flights priced at just US$77.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is American Airlines.
    · Set up price alerts to easily monitor ticket prices without having to check every day.
    · Check Trip.com flight deals and promo codes frequently.
    · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around July.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Indianapolis to Chicago is October, when demand for travel is lower.
  • After crunching the numbers on our May flight calendar, it's currently cheapest to fly from Indianapolis to Chicago on May 20, 2026 with American Airlines, with prices starting at US$80.
  • You can land at any one of the following hubs in Chicago, with Indianapolis International Airport to Chicago O'Hare International Airport (IND-ORD) is by far the most common option on this route: Chicago Midway International Airport (MDW) Chicago O'Hare International Airport (ORD) Chicago Rockford International Airport (RFD).
  • The time difference between Chicago and Indianapolis is 1h.
  • Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

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Note: Prices shown on this page are the estimated lowest prices found in the last 24 hours and include all taxes and fees.

Book with no extra fees

Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are clearly shown before you pay. Charges for checked baggage, onboard meals, Wi‑Fi, and other optional services are also included where applicable in the flight cards.

Real-time pricing updates

Prices, availability, and travel details on this page have been updated within the last 24 hours, and for many routes are refreshed in real time. The more popular the route, the more accurate and up-to-date the data.

Change & Cancellation Policy

Trip.com shows the change and cancellation rules for each ticket during the booking process, including all related fees and conditions. Please refer to the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.