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Indianapolis → Chicago

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IND → MDW1 adulteconomy

9 flight options · 2 airlines

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
5:30 pmIND
1h 10m
Nonstop
5:40 pmMDW
Southwest Airlines
9:50 amMDW
1h
Nonstop
11:50 amIND

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Delta Air Lines
6:43 amIND
4h 3m
DTW · 1h 15m
9:46 amMDW
Delta Air Lines
1:31 pmMDW
5h 2m
DTW · 2h 26m
7:33 pmIND

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
6:45 amIND
1h 10m
Nonstop
6:55 amMDW
Southwest Airlines
9:45 amMDW
1h
Nonstop
11:45 amIND

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
6:45 amIND
1h 10m
Nonstop
6:55 amMDW
Southwest Airlines
9:50 amMDW
1h
Nonstop
11:50 amIND

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
5:30 pmIND
1h 10m
Nonstop
5:40 pmMDW
Southwest Airlines
9:45 amMDW
1h
Nonstop
11:45 amIND

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Delta Air Lines
6:43 amIND
4h 3m
DTW · 1h 15m
9:46 amMDW
Delta Air Lines
1:31 pmMDW
5h 2m
DTW · 2h 26m
7:33 pmIND

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
6:45 amIND
1h 10m
Nonstop
6:55 amMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
6:43 amIND
4h 3m
DTW · 1h 15m
9:46 amMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
5:30 pmIND
1h 10m
Nonstop
5:40 pmMDW

One-way total · 1 adult · Taxes included

Make this trip yours

IND ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Southwest Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • 24-hour cancellationCancel within 24 hours of booking for a full refund when your departure is at least 7 days away. Closer to departure, the airline’s fare rules apply. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

More dates

Nov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-11-20 · one waySouthwest AirlinesWN368$135.002026-10-29T01:14:21Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2224 / WN2314$255.002026-10-29T01:14:21Z
2026-11-20 · one wayDelta Air LinesDL4634 + DL4684$205.002026-10-29T01:14:21Z
2026-11-20 → 2026-11-23Delta Air LinesDL4634 + DL4684 / DL4688 + DL4957$385.002026-10-29T01:14:21Z
2026-11-27 → 2026-12-04Southwest AirlinesWN368 / WN2314$286.882026-10-29T01:14:21Z
2026-11-20 · one waySouthwest AirlinesWN2224$135.002026-10-29T01:14:21Z
2026-11-20 → 2026-11-23Southwest AirlinesWN368 / WN2314$255.002026-10-29T01:14:21Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2224 / WN2314$286.882026-10-29T01:14:21Z
2026-11-27 → 2026-12-04Delta Air LinesDL4634 + DL4684 / DL4688 + DL4957$433.132026-10-29T01:14:21Z

2026-11-20 · one way · $135.00

  • Southwest Airlines WN368: IND 2026-11-20 06:45:00 → MDW 2026-11-20 06:55:00; nonstop; 70 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $255.00

  • Southwest Airlines WN2224: IND 2026-11-20 17:30:00 → MDW 2026-11-20 17:40:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2314: MDW 2026-11-23 09:50:00 → IND 2026-11-23 11:50:00; nonstop; 60 minutes. Local airport times.

2026-11-20 · one way · $205.00

  • Delta Air Lines DL4634 / DL4684: IND 2026-11-20 06:43:00 → MDW 2026-11-20 09:46:00; 1 stop(s) via DTW; 243 minutes. Local airport times.
    • DL4634: IND 2026-11-20 06:43:00 → DTW 2026-11-20 07:55:00; layover at DTW: 75 minutes.
    • DL4684: DTW 2026-11-20 09:10:00 → MDW 2026-11-20 09:46:00.

2026-11-20 → 2026-11-23 · $385.00

  • Delta Air Lines DL4634 / DL4684: IND 2026-11-20 06:43:00 → MDW 2026-11-20 09:46:00; 1 stop(s) via DTW; 243 minutes. Local airport times.
    • DL4634: IND 2026-11-20 06:43:00 → DTW 2026-11-20 07:55:00; layover at DTW: 75 minutes.
    • DL4684: DTW 2026-11-20 09:10:00 → MDW 2026-11-20 09:46:00.
  • Delta Air Lines DL4688 / DL4957: MDW 2026-11-23 13:31:00 → IND 2026-11-23 19:33:00; 1 stop(s) via DTW; 302 minutes. Local airport times.
    • DL4688: MDW 2026-11-23 13:31:00 → DTW 2026-11-23 15:44:00; layover at DTW: 146 minutes.
    • DL4957: DTW 2026-11-23 18:10:00 → IND 2026-11-23 19:33:00.

2026-11-27 → 2026-12-04 · $286.88

  • Southwest Airlines WN368: IND 2026-11-27 06:45:00 → MDW 2026-11-27 06:55:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2314: MDW 2026-12-04 09:45:00 → IND 2026-12-04 11:45:00; nonstop; 60 minutes. Local airport times.

2026-11-20 · one way · $135.00

  • Southwest Airlines WN2224: IND 2026-11-20 17:30:00 → MDW 2026-11-20 17:40:00; nonstop; 70 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $255.00

  • Southwest Airlines WN368: IND 2026-11-20 06:45:00 → MDW 2026-11-20 06:55:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2314: MDW 2026-11-23 09:50:00 → IND 2026-11-23 11:50:00; nonstop; 60 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $286.88

  • Southwest Airlines WN2224: IND 2026-11-27 17:30:00 → MDW 2026-11-27 17:40:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2314: MDW 2026-12-04 09:45:00 → IND 2026-12-04 11:45:00; nonstop; 60 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $433.13

  • Delta Air Lines DL4634 / DL4684: IND 2026-11-27 06:43:00 → MDW 2026-11-27 09:46:00; 1 stop(s) via DTW; 243 minutes. Local airport times.
    • DL4634: IND 2026-11-27 06:43:00 → DTW 2026-11-27 07:55:00; layover at DTW: 75 minutes.
    • DL4684: DTW 2026-11-27 09:10:00 → MDW 2026-11-27 09:46:00.
  • Delta Air Lines DL4688 / DL4957: MDW 2026-12-04 13:31:00 → IND 2026-12-04 19:33:00; 1 stop(s) via DTW; 302 minutes. Local airport times.
    • DL4688: MDW 2026-12-04 13:31:00 → DTW 2026-12-04 15:44:00; layover at DTW: 146 minutes.
    • DL4957: DTW 2026-12-04 18:10:00 → IND 2026-12-04 19:33:00.

More dates for this route