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Route overview: Indianapolis to Chicago (MDW) flight deals

Indianapolis (IND) to Chicago (MDW), Dec 18–20, 2026, return Dec 25–27, 2026: from $281 round trip

Indianapolis (IND) to Chicago (MDW), Dec 18–20, 2026, return Dec 25–27, 2026: from $281 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $281 round trip, Axel-exclusive, Southwest Airlines, nonstop, Dec 18–25, 2026, 1 adult, economy, checked Oct 29, 2026.

IND → MDW1 adulteconomyRound trip

27 flight options · 2 airlines

Nonstop flights

Fri, Dec 18 – Fri, Dec 25

Southwest Airlines
5:30 amIND
1h 10m
Nonstop
5:40 amMDW
Southwest Airlines
9:25 pmMDW
1h 10m
Nonstop
11:35 pmIND

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sun, Dec 27

Southwest Airlines
5:40 pmIND
1h 10m
Nonstop
5:50 pmMDW
Southwest Airlines
9:45 amMDW
1h
Nonstop
11:45 amIND

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sat, Dec 26

Southwest Airlines
5:30 amIND
1h 10m
Nonstop
5:40 amMDW
Southwest Airlines
9:25 pmMDW
1h 10m
Nonstop
11:35 pmIND

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Fri, Dec 25

Southwest Airlines
5:40 pmIND
1h 10m
Nonstop
5:50 pmMDW
Southwest Airlines
9:25 pmMDW
1h 10m
Nonstop
11:35 pmIND

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sat, Dec 26

Southwest Airlines
5:30 amIND
1h 10m
Nonstop
5:40 amMDW
Southwest Airlines
9:25 pmMDW
1h 10m
Nonstop
11:35 pmIND

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Dec 27

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

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sat, Dec 26

Southwest Airlines
5:40 pmIND
1h 10m
Nonstop
5:50 pmMDW
Southwest Airlines
9:25 pmMDW
1h 10m
Nonstop
11:35 pmIND

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Fri, Dec 25

Southwest Airlines
5:30 amIND
1h 10m
Nonstop
5:40 amMDW
Southwest Airlines
9:25 pmMDW
1h 10m
Nonstop
11:35 pmIND

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Fri, Dec 25

Southwest Airlines
4:50 pmIND
1h 15m
Nonstop
5:05 pmMDW
Southwest Airlines
9:25 pmMDW
1h 10m
Nonstop
11:35 pmIND

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sun, Dec 27

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

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sat, Dec 26

Southwest Airlines
4:50 pmIND
1h 15m
Nonstop
5:05 pmMDW
Southwest Airlines
9:25 pmMDW
1h 10m
Nonstop
11:35 pmIND

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sun, Dec 27

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

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Fri, Dec 25

Southwest Airlines
5:30 amIND
1h 10m
Nonstop
5:40 amMDW
Southwest Airlines
9:25 pmMDW
1h 10m
Nonstop
11:35 pmIND

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Dec 18 – Sun, Dec 27

Southwest Airlines
4:50 pmIND
1h 15m
Nonstop
5:05 pmMDW
Southwest Airlines
9:45 amMDW
1h
Nonstop
11:45 amIND

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Dec 19 – Sat, Dec 26

Southwest Airlines
5:40 pmIND
1h 10m
Nonstop
5:50 pmMDW
Southwest Airlines
9:25 pmMDW
1h 10m
Nonstop
11:35 pmIND

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Dec 27

Southwest Airlines
5:40 pmIND
1h 10m
Nonstop
5:50 pmMDW
Southwest Airlines
9:45 amMDW
1h
Nonstop
11:45 amIND

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Fri, Dec 25

Southwest Airlines
5:40 pmIND
1h 10m
Nonstop
5:50 pmMDW
Southwest Airlines
9:25 pmMDW
1h 10m
Nonstop
11:35 pmIND

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sun, Dec 20 – Sat, Dec 26

Southwest Airlines
5:30 amIND
1h 10m
Nonstop
5:40 amMDW
Southwest Airlines
9:25 pmMDW
1h 10m
Nonstop
11:35 pmIND

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Fri, Dec 18 – Sun, Dec 27

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

Availability is checked when you select these flights.

Sat, Dec 19 – Sat, Dec 26

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

Availability is checked when you select these flights.

Sat, Dec 19 – Sun, Dec 27

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

Availability is checked when you select these flights.

Fri, Dec 18 – Fri, Dec 25

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

Availability is checked when you select these flights.

Fri, Dec 18 – Sat, Dec 26

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

Availability is checked when you select these flights.

Sat, Dec 19 – Fri, Dec 25

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

Availability is checked when you select these flights.

Sun, Dec 20 – Sun, Dec 27

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

Availability is checked when you select these flights.

Sun, Dec 20 – Sat, Dec 26

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

Availability is checked when you select these flights.

Sun, Dec 20 – Fri, Dec 25

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

Availability is checked when you select these flights.

Hotels for these nights (Dec 18–25, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey $700 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $233 · 5★ Sofitel Chicago Magnificent Mile $1,675

Hotels for these nights (Dec 18–26, 2026 · 8 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection $824 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $343 · 5★ Sofitel Chicago Magnificent Mile $1,889

Hotels for these nights (Dec 18–27, 2026 · 9 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection $941 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $385 · 5★ Sofitel Chicago Magnificent Mile $2,098

Hotels for these nights (Dec 19–25, 2026 · 6 nights · 2 adults, 1 room): 3★ Hotel Versey $581 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $164 · 5★ Sofitel Chicago Magnificent Mile $1,473

Hotels for these nights (Dec 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey $712 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $274 · 5★ Sofitel Chicago Magnificent Mile $1,687

Hotels for these nights (Dec 19–27, 2026 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $804 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $316 · 5★ Sofitel Chicago Magnificent Mile $1,896

Hotels for these nights (Dec 20–25, 2026 · 5 nights · 2 adults, 1 room): 3★ Hotel Versey $462 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $95 · 5★ Sofitel Chicago Magnificent Mile $1,159

Hotels for these nights (Dec 20–26, 2026 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $583 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $205 · 5★ Sofitel Chicago Magnificent Mile $1,373

Hotels for these nights (Dec 20–27, 2026 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North $674 · 4★ The Chicago Hotel Collection Ambassador Gold Coast $247 · 5★ Sofitel Chicago Magnificent Mile $1,582

Make this trip yours

IND ⇄ MDW

Economy

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Explore this route

All dates for this routeHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

Indianapolis (IND) to Chicago (MDW), Dec 18–20, 2026, return Dec 25–27, 2026: from $281 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $281 round trip, Axel-exclusive, Southwest Airlines, nonstop, Dec 18–25, 2026, 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Exact travel datesAirlineFlightsTimes, duration, stopsTotal pricePrice issued (UTC)
2026-12-18 → 2026-12-25Southwest AirlinesWN2223 / WN216305:30:00→05:40:00 1h 10m nonstop · 21:25:00→23:35:00 1h 10m nonstopAxel-exclusive $280.502026-10-29T01:14:21Z
2026-12-18 → 2026-12-27Delta Air LinesDL4634 + DL4684 / DL4688 + DL495706:43:00→09:46:00 4h 03m 1 stop via DTW · 13:31:00→19:33:00 5h 02m 1 stop via DTWAxel-exclusive $423.502026-10-29T01:14:21Z
2026-12-19 → 2026-12-27Southwest AirlinesWN2224 / WN231417:40:00→17:50:00 1h 10m nonstop · 09:45:00→11:45:00 1h 00m nonstopAxel-exclusive $280.502026-10-29T01:14:21Z
2026-12-18 → 2026-12-26Southwest AirlinesWN2223 / WN216305:30:00→05:40:00 1h 10m nonstop · 21:25:00→23:35:00 1h 10m nonstopAxel-exclusive $280.502026-10-29T01:14:21Z
2026-12-19 → 2026-12-25Southwest AirlinesWN2224 / WN216317:40:00→17:50:00 1h 10m nonstop · 21:25:00→23:35:00 1h 10m nonstopAxel-exclusive $280.502026-10-29T01:14:21Z
2026-12-19 → 2026-12-26Southwest AirlinesWN2223 / WN216305:30:00→05:40:00 1h 10m nonstop · 21:25:00→23:35:00 1h 10m nonstopAxel-exclusive $280.502026-10-29T01:14:21Z
2026-12-20 → 2026-12-27Southwest AirlinesWN2223 / WN231405:30:00→05:40:00 1h 10m nonstop · 09:45:00→11:45:00 1h 00m nonstopAxel-exclusive $306.002026-10-29T01:14:21Z
2026-12-20 → 2026-12-26Southwest AirlinesWN2224 / WN216317:40:00→17:50:00 1h 10m nonstop · 21:25:00→23:35:00 1h 10m nonstopAxel-exclusive $306.002026-10-29T01:14:21Z
2026-12-20 → 2026-12-25Southwest AirlinesWN2223 / WN216305:30:00→05:40:00 1h 10m nonstop · 21:25:00→23:35:00 1h 10m nonstopAxel-exclusive $306.002026-10-29T01:14:21Z
2026-12-18 → 2026-12-25Southwest AirlinesWN346 / WN216316:50:00→17:05:00 1h 15m nonstop · 21:25:00→23:35:00 1h 10m nonstopAxel-exclusive $280.502026-10-29T01:14:21Z
2026-12-19 → 2026-12-27Southwest AirlinesWN2223 / WN231405:30:00→05:40:00 1h 10m nonstop · 09:45:00→11:45:00 1h 00m nonstopAxel-exclusive $280.502026-10-29T01:14:21Z
2026-12-18 → 2026-12-26Southwest AirlinesWN346 / WN216316:50:00→17:05:00 1h 15m nonstop · 21:25:00→23:35:00 1h 10m nonstopAxel-exclusive $280.502026-10-29T01:14:21Z
2026-12-18 → 2026-12-27Southwest AirlinesWN2223 / WN231405:30:00→05:40:00 1h 10m nonstop · 09:45:00→11:45:00 1h 00m nonstopAxel-exclusive $280.502026-10-29T01:14:21Z
2026-12-19 → 2026-12-25Southwest AirlinesWN2223 / WN216305:30:00→05:40:00 1h 10m nonstop · 21:25:00→23:35:00 1h 10m nonstopAxel-exclusive $280.502026-10-29T01:14:21Z
2026-12-18 → 2026-12-27Southwest AirlinesWN346 / WN231416:50:00→17:05:00 1h 15m nonstop · 09:45:00→11:45:00 1h 00m nonstopAxel-exclusive $280.502026-10-29T01:14:21Z
2026-12-19 → 2026-12-26Southwest AirlinesWN2224 / WN216317:40:00→17:50:00 1h 10m nonstop · 21:25:00→23:35:00 1h 10m nonstopAxel-exclusive $280.502026-10-29T01:14:21Z
2026-12-20 → 2026-12-27Southwest AirlinesWN2224 / WN231417:40:00→17:50:00 1h 10m nonstop · 09:45:00→11:45:00 1h 00m nonstopAxel-exclusive $306.002026-10-29T01:14:21Z
2026-12-20 → 2026-12-25Southwest AirlinesWN2224 / WN216317:40:00→17:50:00 1h 10m nonstop · 21:25:00→23:35:00 1h 10m nonstopAxel-exclusive $306.002026-10-29T01:14:21Z
2026-12-20 → 2026-12-26Southwest AirlinesWN2223 / WN216305:30:00→05:40:00 1h 10m nonstop · 21:25:00→23:35:00 1h 10m nonstopAxel-exclusive $306.002026-10-29T01:14:21Z
2026-12-19 → 2026-12-26Delta Air LinesDL4634 + DL4684 / DL4688 + DL495706:43:00→09:46:00 4h 03m 1 stop via DTW · 13:31:00→19:33:00 5h 02m 1 stop via DTWAxel-exclusive $423.502026-10-29T01:14:21Z
2026-12-19 → 2026-12-27Delta Air LinesDL4634 + DL4684 / DL4688 + DL495706:43:00→09:46:00 4h 03m 1 stop via DTW · 13:31:00→19:33:00 5h 02m 1 stop via DTWAxel-exclusive $423.502026-10-29T01:14:21Z
2026-12-18 → 2026-12-25Delta Air LinesDL4634 + DL4684 / DL4688 + DL495706:43:00→09:46:00 4h 03m 1 stop via DTW · 13:31:00→19:33:00 5h 02m 1 stop via DTWAxel-exclusive $423.502026-10-29T01:14:21Z
2026-12-18 → 2026-12-26Delta Air LinesDL4634 + DL4684 / DL4688 + DL495706:43:00→09:46:00 4h 03m 1 stop via DTW · 13:31:00→19:33:00 5h 02m 1 stop via DTWAxel-exclusive $423.502026-10-29T01:14:21Z
2026-12-19 → 2026-12-25Delta Air LinesDL4634 + DL4684 / DL4688 + DL495706:43:00→09:46:00 4h 03m 1 stop via DTW · 13:31:00→19:33:00 5h 02m 1 stop via DTWAxel-exclusive $423.502026-10-29T01:14:21Z
2026-12-20 → 2026-12-27Delta Air LinesDL4634 + DL4684 / DL4688 + DL495706:43:00→09:46:00 4h 03m 1 stop via DTW · 13:31:00→19:33:00 5h 02m 1 stop via DTWAxel-exclusive $462.002026-10-29T01:14:21Z
2026-12-20 → 2026-12-26Delta Air LinesDL4634 + DL4684 / DL4688 + DL495706:43:00→09:46:00 4h 03m 1 stop via DTW · 13:31:00→19:33:00 5h 02m 1 stop via DTWAxel-exclusive $462.002026-10-29T01:14:21Z
2026-12-20 → 2026-12-25Delta Air LinesDL4634 + DL4684 / DL4688 + DL495706:43:00→09:46:00 4h 03m 1 stop via DTW · 13:31:00→19:33:00 5h 02m 1 stop via DTWAxel-exclusive $462.002026-10-29T01:14:21Z

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

All hotels in Chicago

Route overview: Indianapolis to Chicago (MDW) flight deals

2026-12-18 → 2026-12-25 · Axel-exclusive $280.50

  • Southwest Airlines WN2223: IND 2026-12-18 05:30:00 → MDW 2026-12-18 05:40:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2163: MDW 2026-12-25 21:25:00 → IND 2026-12-25 23:35:00; nonstop; 70 minutes. Local airport times.

2026-12-18 → 2026-12-27 · Axel-exclusive $423.50

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

2026-12-19 → 2026-12-27 · Axel-exclusive $280.50

  • Southwest Airlines WN2224: IND 2026-12-19 17:40:00 → MDW 2026-12-19 17:50:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2314: MDW 2026-12-27 09:45:00 → IND 2026-12-27 11:45:00; nonstop; 60 minutes. Local airport times.

2026-12-18 → 2026-12-26 · Axel-exclusive $280.50

  • Southwest Airlines WN2223: IND 2026-12-18 05:30:00 → MDW 2026-12-18 05:40:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2163: MDW 2026-12-26 21:25:00 → IND 2026-12-26 23:35:00; nonstop; 70 minutes. Local airport times.

2026-12-19 → 2026-12-25 · Axel-exclusive $280.50

  • Southwest Airlines WN2224: IND 2026-12-19 17:40:00 → MDW 2026-12-19 17:50:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2163: MDW 2026-12-25 21:25:00 → IND 2026-12-25 23:35:00; nonstop; 70 minutes. Local airport times.

2026-12-19 → 2026-12-26 · Axel-exclusive $280.50

  • Southwest Airlines WN2223: IND 2026-12-19 05:30:00 → MDW 2026-12-19 05:40:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2163: MDW 2026-12-26 21:25:00 → IND 2026-12-26 23:35:00; nonstop; 70 minutes. Local airport times.

2026-12-20 → 2026-12-27 · Axel-exclusive $306.00

  • Southwest Airlines WN2223: IND 2026-12-20 05:30:00 → MDW 2026-12-20 05:40:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2314: MDW 2026-12-27 09:45:00 → IND 2026-12-27 11:45:00; nonstop; 60 minutes. Local airport times.

2026-12-20 → 2026-12-26 · Axel-exclusive $306.00

  • Southwest Airlines WN2224: IND 2026-12-20 17:40:00 → MDW 2026-12-20 17:50:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2163: MDW 2026-12-26 21:25:00 → IND 2026-12-26 23:35:00; nonstop; 70 minutes. Local airport times.

2026-12-20 → 2026-12-25 · Axel-exclusive $306.00

  • Southwest Airlines WN2223: IND 2026-12-20 05:30:00 → MDW 2026-12-20 05:40:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2163: MDW 2026-12-25 21:25:00 → IND 2026-12-25 23:35:00; nonstop; 70 minutes. Local airport times.

2026-12-18 → 2026-12-25 · Axel-exclusive $280.50

  • Southwest Airlines WN346: IND 2026-12-18 16:50:00 → MDW 2026-12-18 17:05:00; nonstop; 75 minutes. Local airport times.
  • Southwest Airlines WN2163: MDW 2026-12-25 21:25:00 → IND 2026-12-25 23:35:00; nonstop; 70 minutes. Local airport times.

2026-12-19 → 2026-12-27 · Axel-exclusive $280.50

  • Southwest Airlines WN2223: IND 2026-12-19 05:30:00 → MDW 2026-12-19 05:40:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2314: MDW 2026-12-27 09:45:00 → IND 2026-12-27 11:45:00; nonstop; 60 minutes. Local airport times.

2026-12-18 → 2026-12-26 · Axel-exclusive $280.50

  • Southwest Airlines WN346: IND 2026-12-18 16:50:00 → MDW 2026-12-18 17:05:00; nonstop; 75 minutes. Local airport times.
  • Southwest Airlines WN2163: MDW 2026-12-26 21:25:00 → IND 2026-12-26 23:35:00; nonstop; 70 minutes. Local airport times.

2026-12-18 → 2026-12-27 · Axel-exclusive $280.50

  • Southwest Airlines WN2223: IND 2026-12-18 05:30:00 → MDW 2026-12-18 05:40:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2314: MDW 2026-12-27 09:45:00 → IND 2026-12-27 11:45:00; nonstop; 60 minutes. Local airport times.

2026-12-19 → 2026-12-25 · Axel-exclusive $280.50

  • Southwest Airlines WN2223: IND 2026-12-19 05:30:00 → MDW 2026-12-19 05:40:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2163: MDW 2026-12-25 21:25:00 → IND 2026-12-25 23:35:00; nonstop; 70 minutes. Local airport times.

2026-12-18 → 2026-12-27 · Axel-exclusive $280.50

  • Southwest Airlines WN346: IND 2026-12-18 16:50:00 → MDW 2026-12-18 17:05:00; nonstop; 75 minutes. Local airport times.
  • Southwest Airlines WN2314: MDW 2026-12-27 09:45:00 → IND 2026-12-27 11:45:00; nonstop; 60 minutes. Local airport times.

2026-12-19 → 2026-12-26 · Axel-exclusive $280.50

  • Southwest Airlines WN2224: IND 2026-12-19 17:40:00 → MDW 2026-12-19 17:50:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2163: MDW 2026-12-26 21:25:00 → IND 2026-12-26 23:35:00; nonstop; 70 minutes. Local airport times.

2026-12-20 → 2026-12-27 · Axel-exclusive $306.00

  • Southwest Airlines WN2224: IND 2026-12-20 17:40:00 → MDW 2026-12-20 17:50:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2314: MDW 2026-12-27 09:45:00 → IND 2026-12-27 11:45:00; nonstop; 60 minutes. Local airport times.

2026-12-20 → 2026-12-25 · Axel-exclusive $306.00

  • Southwest Airlines WN2224: IND 2026-12-20 17:40:00 → MDW 2026-12-20 17:50:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2163: MDW 2026-12-25 21:25:00 → IND 2026-12-25 23:35:00; nonstop; 70 minutes. Local airport times.

2026-12-20 → 2026-12-26 · Axel-exclusive $306.00

  • Southwest Airlines WN2223: IND 2026-12-20 05:30:00 → MDW 2026-12-20 05:40:00; nonstop; 70 minutes. Local airport times.
  • Southwest Airlines WN2163: MDW 2026-12-26 21:25:00 → IND 2026-12-26 23:35:00; nonstop; 70 minutes. Local airport times.

2026-12-19 → 2026-12-26 · Axel-exclusive $423.50

  • Delta Air Lines DL4634 / DL4684: IND 2026-12-19 06:43:00 → MDW 2026-12-19 09:46:00; 1 stop(s) via DTW; 243 minutes. Local airport times.
    • DL4634: IND 2026-12-19 06:43:00 → DTW 2026-12-19 07:55:00; layover at DTW: 75 minutes.
    • DL4684: DTW 2026-12-19 09:10:00 → MDW 2026-12-19 09:46:00.
  • Delta Air Lines DL4688 / DL4957: MDW 2026-12-26 13:31:00 → IND 2026-12-26 19:33:00; 1 stop(s) via DTW; 302 minutes. Local airport times.
    • DL4688: MDW 2026-12-26 13:31:00 → DTW 2026-12-26 15:44:00; layover at DTW: 146 minutes.
    • DL4957: DTW 2026-12-26 18:10:00 → IND 2026-12-26 19:33:00.

2026-12-19 → 2026-12-27 · Axel-exclusive $423.50

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

2026-12-18 → 2026-12-25 · Axel-exclusive $423.50

  • Delta Air Lines DL4634 / DL4684: IND 2026-12-18 06:43:00 → MDW 2026-12-18 09:46:00; 1 stop(s) via DTW; 243 minutes. Local airport times.
    • DL4634: IND 2026-12-18 06:43:00 → DTW 2026-12-18 07:55:00; layover at DTW: 75 minutes.
    • DL4684: DTW 2026-12-18 09:10:00 → MDW 2026-12-18 09:46:00.
  • Delta Air Lines DL4688 / DL4957: MDW 2026-12-25 13:31:00 → IND 2026-12-25 19:33:00; 1 stop(s) via DTW; 302 minutes. Local airport times.
    • DL4688: MDW 2026-12-25 13:31:00 → DTW 2026-12-25 15:44:00; layover at DTW: 146 minutes.
    • DL4957: DTW 2026-12-25 18:10:00 → IND 2026-12-25 19:33:00.

2026-12-18 → 2026-12-26 · Axel-exclusive $423.50

  • Delta Air Lines DL4634 / DL4684: IND 2026-12-18 06:43:00 → MDW 2026-12-18 09:46:00; 1 stop(s) via DTW; 243 minutes. Local airport times.
    • DL4634: IND 2026-12-18 06:43:00 → DTW 2026-12-18 07:55:00; layover at DTW: 75 minutes.
    • DL4684: DTW 2026-12-18 09:10:00 → MDW 2026-12-18 09:46:00.
  • Delta Air Lines DL4688 / DL4957: MDW 2026-12-26 13:31:00 → IND 2026-12-26 19:33:00; 1 stop(s) via DTW; 302 minutes. Local airport times.
    • DL4688: MDW 2026-12-26 13:31:00 → DTW 2026-12-26 15:44:00; layover at DTW: 146 minutes.
    • DL4957: DTW 2026-12-26 18:10:00 → IND 2026-12-26 19:33:00.

2026-12-19 → 2026-12-25 · Axel-exclusive $423.50

  • Delta Air Lines DL4634 / DL4684: IND 2026-12-19 06:43:00 → MDW 2026-12-19 09:46:00; 1 stop(s) via DTW; 243 minutes. Local airport times.
    • DL4634: IND 2026-12-19 06:43:00 → DTW 2026-12-19 07:55:00; layover at DTW: 75 minutes.
    • DL4684: DTW 2026-12-19 09:10:00 → MDW 2026-12-19 09:46:00.
  • Delta Air Lines DL4688 / DL4957: MDW 2026-12-25 13:31:00 → IND 2026-12-25 19:33:00; 1 stop(s) via DTW; 302 minutes. Local airport times.
    • DL4688: MDW 2026-12-25 13:31:00 → DTW 2026-12-25 15:44:00; layover at DTW: 146 minutes.
    • DL4957: DTW 2026-12-25 18:10:00 → IND 2026-12-25 19:33:00.

2026-12-20 → 2026-12-27 · Axel-exclusive $462.00

  • Delta Air Lines DL4634 / DL4684: IND 2026-12-20 06:43:00 → MDW 2026-12-20 09:46:00; 1 stop(s) via DTW; 243 minutes. Local airport times.
    • DL4634: IND 2026-12-20 06:43:00 → DTW 2026-12-20 07:55:00; layover at DTW: 75 minutes.
    • DL4684: DTW 2026-12-20 09:10:00 → MDW 2026-12-20 09:46:00.
  • Delta Air Lines DL4688 / DL4957: MDW 2026-12-27 13:31:00 → IND 2026-12-27 19:33:00; 1 stop(s) via DTW; 302 minutes. Local airport times.
    • DL4688: MDW 2026-12-27 13:31:00 → DTW 2026-12-27 15:44:00; layover at DTW: 146 minutes.
    • DL4957: DTW 2026-12-27 18:10:00 → IND 2026-12-27 19:33:00.

2026-12-20 → 2026-12-26 · Axel-exclusive $462.00

  • Delta Air Lines DL4634 / DL4684: IND 2026-12-20 06:43:00 → MDW 2026-12-20 09:46:00; 1 stop(s) via DTW; 243 minutes. Local airport times.
    • DL4634: IND 2026-12-20 06:43:00 → DTW 2026-12-20 07:55:00; layover at DTW: 75 minutes.
    • DL4684: DTW 2026-12-20 09:10:00 → MDW 2026-12-20 09:46:00.
  • Delta Air Lines DL4688 / DL4957: MDW 2026-12-26 13:31:00 → IND 2026-12-26 19:33:00; 1 stop(s) via DTW; 302 minutes. Local airport times.
    • DL4688: MDW 2026-12-26 13:31:00 → DTW 2026-12-26 15:44:00; layover at DTW: 146 minutes.
    • DL4957: DTW 2026-12-26 18:10:00 → IND 2026-12-26 19:33:00.

2026-12-20 → 2026-12-25 · Axel-exclusive $462.00

  • Delta Air Lines DL4634 / DL4684: IND 2026-12-20 06:43:00 → MDW 2026-12-20 09:46:00; 1 stop(s) via DTW; 243 minutes. Local airport times.
    • DL4634: IND 2026-12-20 06:43:00 → DTW 2026-12-20 07:55:00; layover at DTW: 75 minutes.
    • DL4684: DTW 2026-12-20 09:10:00 → MDW 2026-12-20 09:46:00.
  • Delta Air Lines DL4688 / DL4957: MDW 2026-12-25 13:31:00 → IND 2026-12-25 19:33:00; 1 stop(s) via DTW; 302 minutes. Local airport times.
    • DL4688: MDW 2026-12-25 13:31:00 → DTW 2026-12-25 15:44:00; layover at DTW: 146 minutes.
    • DL4957: DTW 2026-12-25 18:10:00 → IND 2026-12-25 19:33:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

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  • This page: Indianapolis (IND) to Chicago (MDW) · Dec 18–Dec 20, 2026 · return Dec 25–Dec 27, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
  • Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Indianapolis to Chicago (MDW) flight deals · Flight search guide.
  • Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.