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Nashville → Chicago

Jan 21, 2027 · return Jan 27, 2027

BNA → MDW1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Thu, Jan 21 – Wed, Jan 27

Southwest Airlines
2:45 pmBNA
1h 30m
Nonstop
4:15 pmMDW
Southwest Airlines
10:00 amMDW
1h 25m
Nonstop
11:25 amBNA

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Wed, Jan 27

Southwest Airlines
11:25 amBNA
1h 30m
Nonstop
12:55 pmMDW
Southwest Airlines
10:00 amMDW
1h 25m
Nonstop
11:25 amBNA

Round-trip total · 1 adult · Taxes included

One-stop flights

Thu, Jan 21 – Wed, Jan 27

Southwest Airlines
6:25 amBNA
5h 40m
STL · 3h 15m
12:05 pmMDW
Southwest Airlines
10:00 amMDW
1h 25m
Nonstop
11:25 amBNA

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Wed, Jan 27

Southwest Airlines
9:00 amBNA
5h 30m
CLE · 2h 25m
2:30 pmMDW
Southwest Airlines
10:00 amMDW
1h 25m
Nonstop
11:25 amBNA

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Wed, Jan 27

Southwest Airlines
1:25 pmBNA
4h 25m
IND · 2h 5m
5:50 pmMDW
Southwest Airlines
10:00 amMDW
1h 25m
Nonstop
11:25 amBNA

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Wed, Jan 27

Southwest Airlines
10:15 amBNA
4h 45m
CMH · 2h 15m
3:00 pmMDW
Southwest Airlines
10:00 amMDW
1h 25m
Nonstop
11:25 amBNA

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Wed, Jan 27

Southwest Airlines
3:20 pmBNA
4h 35m
DTW · 1h 35m
7:55 pmMDW
Southwest Airlines
10:00 amMDW
1h 25m
Nonstop
11:25 amBNA

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Wed, Jan 27

Southwest Airlines
10:15 amBNA
4h 10m
SDF · 1h 55m
2:25 pmMDW
Southwest Airlines
10:00 amMDW
1h 25m
Nonstop
11:25 amBNA

Round-trip total · 1 adult · Taxes included

Make this trip yours

BNA ⇄ MDW

Economy

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

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More dates

All dates for this routeNov 24, 2026 → Nov 29, 2026Dec 22, 2026 → Dec 27, 2026Dec 30, 2026 → Jan 2, 2027Jan 15, 2027 → Jan 18, 2027Oct 30, 2026 → Nov 2, 2026Oct 31, 2026 → Nov 7, 2026Nov 27, 2026 → Nov 30, 2026Nov 28, 2026 → Dec 5, 2026Dec 25, 2026 → Dec 28, 2026Dec 26, 2026 → Jan 2, 2027Jan 22, 2027 → Jan 25, 2027Oct 30, 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)
2027-01-21 → 2027-01-27Southwest AirlinesWN2062 / WN1400$230.002026-10-29T00:50:05Z
2027-01-21 → 2027-01-27Southwest AirlinesWN1005 / WN1400$230.002026-10-29T00:50:05Z
2027-01-21 → 2027-01-27Southwest AirlinesWN738 + WN287 / WN1400$240.002026-10-29T00:50:05Z
2027-01-21 → 2027-01-27Southwest AirlinesWN4398 + WN1219 / WN1400$240.002026-10-29T00:50:05Z
2027-01-21 → 2027-01-27Southwest AirlinesWN578 + WN2224 / WN1400$240.002026-10-29T00:50:05Z
2027-01-21 → 2027-01-27Southwest AirlinesWN2145 + WN2988 / WN1400$240.002026-10-29T00:50:05Z
2027-01-21 → 2027-01-27Southwest AirlinesWN2971 + WN955 / WN1400$240.002026-10-29T00:50:05Z
2027-01-21 → 2027-01-27Southwest AirlinesWN712 + WN2495 / WN1400$240.002026-10-29T00:50:05Z

2027-01-21 → 2027-01-27 · $230.00

  • Southwest Airlines WN2062: BNA 2027-01-21 14:45:00 → MDW 2027-01-21 16:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN1400: MDW 2027-01-27 10:00:00 → BNA 2027-01-27 11:25:00; nonstop; 85 minutes. Local airport times.

2027-01-21 → 2027-01-27 · $230.00

  • Southwest Airlines WN1005: BNA 2027-01-21 11:25:00 → MDW 2027-01-21 12:55:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN1400: MDW 2027-01-27 10:00:00 → BNA 2027-01-27 11:25:00; nonstop; 85 minutes. Local airport times.

2027-01-21 → 2027-01-27 · $240.00

  • Southwest Airlines WN738 / WN287: BNA 2027-01-21 06:25:00 → MDW 2027-01-21 12:05:00; 1 stop(s) via STL; 340 minutes. Local airport times.
    • WN738: BNA 2027-01-21 06:25:00 → STL 2027-01-21 07:40:00; layover at STL: 195 minutes.
    • WN287: STL 2027-01-21 10:55:00 → MDW 2027-01-21 12:05:00.
  • Southwest Airlines WN1400: MDW 2027-01-27 10:00:00 → BNA 2027-01-27 11:25:00; nonstop; 85 minutes. Local airport times.

2027-01-21 → 2027-01-27 · $240.00

  • Southwest Airlines WN4398 / WN1219: BNA 2027-01-21 09:00:00 → MDW 2027-01-21 14:30:00; 1 stop(s) via CLE; 330 minutes. Local airport times.
    • WN4398: BNA 2027-01-21 09:00:00 → CLE 2027-01-21 11:30:00; layover at CLE: 145 minutes.
    • WN1219: CLE 2027-01-21 13:55:00 → MDW 2027-01-21 14:30:00.
  • Southwest Airlines WN1400: MDW 2027-01-27 10:00:00 → BNA 2027-01-27 11:25:00; nonstop; 85 minutes. Local airport times.

2027-01-21 → 2027-01-27 · $240.00

  • Southwest Airlines WN578 / WN2224: BNA 2027-01-21 13:25:00 → MDW 2027-01-21 17:50:00; 1 stop(s) via IND; 265 minutes. Local airport times.
    • WN578: BNA 2027-01-21 13:25:00 → IND 2027-01-21 15:35:00; layover at IND: 125 minutes.
    • WN2224: IND 2027-01-21 17:40:00 → MDW 2027-01-21 17:50:00.
  • Southwest Airlines WN1400: MDW 2027-01-27 10:00:00 → BNA 2027-01-27 11:25:00; nonstop; 85 minutes. Local airport times.

2027-01-21 → 2027-01-27 · $240.00

  • Southwest Airlines WN2145 / WN2988: BNA 2027-01-21 10:15:00 → MDW 2027-01-21 15:00:00; 1 stop(s) via CMH; 285 minutes. Local airport times.
    • WN2145: BNA 2027-01-21 10:15:00 → CMH 2027-01-21 12:30:00; layover at CMH: 135 minutes.
    • WN2988: CMH 2027-01-21 14:45:00 → MDW 2027-01-21 15:00:00.
  • Southwest Airlines WN1400: MDW 2027-01-27 10:00:00 → BNA 2027-01-27 11:25:00; nonstop; 85 minutes. Local airport times.

2027-01-21 → 2027-01-27 · $240.00

  • Southwest Airlines WN2971 / WN955: BNA 2027-01-21 15:20:00 → MDW 2027-01-21 19:55:00; 1 stop(s) via DTW; 275 minutes. Local airport times.
    • WN2971: BNA 2027-01-21 15:20:00 → DTW 2027-01-21 18:00:00; layover at DTW: 95 minutes.
    • WN955: DTW 2027-01-21 19:35:00 → MDW 2027-01-21 19:55:00.
  • Southwest Airlines WN1400: MDW 2027-01-27 10:00:00 → BNA 2027-01-27 11:25:00; nonstop; 85 minutes. Local airport times.

2027-01-21 → 2027-01-27 · $240.00

  • Southwest Airlines WN712 / WN2495: BNA 2027-01-21 10:15:00 → MDW 2027-01-21 14:25:00; 1 stop(s) via SDF; 250 minutes. Local airport times.
    • WN712: BNA 2027-01-21 10:15:00 → SDF 2027-01-21 12:10:00; layover at SDF: 115 minutes.
    • WN2495: SDF 2027-01-21 14:05:00 → MDW 2027-01-21 14:25:00.
  • Southwest Airlines WN1400: MDW 2027-01-27 10:00:00 → BNA 2027-01-27 11:25:00; nonstop; 85 minutes. Local airport times.

More dates for this route