Chicago (MDW) to Louisville (SDF), Nov 27, 2026: round trips from $318, one way from $208

Chicago (MDW) to Louisville (SDF), Nov 27, 2026: round trips from $318, one way from $208 on Axel, checked Oct 29, 2026. Lowest published fares: $318 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 27, 2026 – Dec 1, 2026; $208 one way, Axel-exclusive, Southwest Airlines, 1 stop, Nov 27, 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.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and issuance times already shown here.

Hotels in Louisville for these trips

Hotels: under a trip, hotels in Louisville 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.

• Hotels in Louisville for these nights (Nov 27–28, 2026 · 1 night · 2 adults, 1 room): 3★ Home2 Suites by Hilton Louisville Downtown NuLu, $95 total · 4★ The Brown Hotel, $124 total
• Hotels in Louisville for these nights (Nov 27–29, 2026 · 2 nights · 2 adults, 1 room): 3★ Home2 Suites by Hilton Louisville Downtown NuLu, $188 total · 4★ The Brown Hotel, $238 total
• Hotels in Louisville for these nights (Nov 27–30, 2026 · 3 nights · 2 adults, 1 room): 3★ Home2 Suites by Hilton Louisville Downtown NuLu, $288 total · 4★ The Brown Hotel, $348 total
• Hotels in Louisville for these nights (Nov 27 – Dec 1, 2026 · 4 nights · 2 adults, 1 room): 3★ Home2 Suites by Hilton Louisville Downtown NuLu, $391 total · 4★ The Brown Hotel, $478 total
• Hotels in Louisville for these nights (Nov 27 – Dec 2, 2026 · 5 nights · 2 adults, 1 room): 3★ Cambria Hotel Louisville Downtown-Whiskey Row, $489 total · 4★ The Brown Hotel, $608 total
• Hotels in Louisville for these nights (Nov 27 – Dec 3, 2026 · 6 nights · 2 adults, 1 room): 3★ Cambria Hotel Louisville Downtown-Whiskey Row, $586 total · 4★ The Brown Hotel, $755 total
• Hotels in Louisville for these nights (Nov 27 – Dec 4, 2026 · 7 nights · 2 adults, 1 room): 3★ Cambria Hotel Louisville Downtown-Whiskey Row, $681 total · 4★ The Brown Hotel, $888 total
• Hotels in Louisville for these nights (Nov 27 – Dec 5, 2026 · 8 nights · 2 adults, 1 room): 3★ Home2 Suites by Hilton Louisville Downtown NuLu, $909 total · 4★ The Brown Hotel, $1,038 total
• Hotels in Louisville for these nights (Nov 27 – Dec 6, 2026 · 9 nights · 2 adults, 1 room): 3★ Cambria Hotel Louisville Downtown-Whiskey Row, $1,100 total · 4★ The Brown Hotel, $1,198 total
• Hotels in Louisville for these nights (Nov 27 – Dec 7, 2026 · 10 nights · 2 adults, 1 room): 3★ Cambria Hotel Louisville Downtown-Whiskey Row, $1,205 total · 4★ The Brown Hotel, $1,328 total
• Hotels in Louisville for these nights (Nov 27 – Dec 8, 2026 · 11 nights · 2 adults, 1 room): 3★ Cambria Hotel Louisville Downtown-Whiskey Row, $1,320 total · 4★ The Brown Hotel, $1,458 total
• Hotels in Louisville for these nights (Nov 27 – Dec 9, 2026 · 12 nights · 2 adults, 1 room): 3★ Cambria Hotel Louisville Downtown-Whiskey Row, $1,431 total · 4★ The Brown Hotel, $1,591 total
• Hotels in Louisville for these nights (Nov 27 – Dec 10, 2026 · 13 nights · 2 adults, 1 room): 3★ Cambria Hotel Louisville Downtown-Whiskey Row, $1,541 total · 4★ The Brown Hotel, $1,717 total
• Hotels in Louisville for these nights (Nov 27 – Dec 11, 2026 · 14 nights · 2 adults, 1 room): 3★ Cambria Hotel Louisville Downtown-Whiskey Row, $1,662 total · 4★ The Brown Hotel, $1,846 total

All hotels in Louisville

Route overview: Chicago to Louisville (SDF) flight deals

2026-11-27 · one way · Axel-exclusive $208.00

• Southwest Airlines WN2897 / WN4368: MDW 2026-11-27 17:25:00 → SDF 2026-11-27 22:45:00; 1 stop(s) via BNA; 260 minutes. Local airport times.
  • WN2897: MDW 2026-11-27 17:25:00 → BNA 2026-11-27 18:50:00; layover at BNA: 110 minutes.
  • WN4368: BNA 2026-11-27 20:40:00 → SDF 2026-11-27 22:45:00.

2026-11-27 → 2026-11-28 · Axel-exclusive $354.25

• Southwest Airlines WN2897 / WN4368: MDW 2026-11-27 17:25:00 → SDF 2026-11-27 22:45:00; 1 stop(s) via BNA; 260 minutes. Local airport times.
  • WN2897: MDW 2026-11-27 17:25:00 → BNA 2026-11-27 18:50:00; layover at BNA: 110 minutes.
  • WN4368: BNA 2026-11-27 20:40:00 → SDF 2026-11-27 22:45:00.
• Southwest Airlines WN2350: SDF 2026-11-28 08:50:00 → MDW 2026-11-28 09:05:00; nonstop; 75 minutes. Local airport times.

2026-11-27 → 2026-11-29 · Axel-exclusive $354.25

• Southwest Airlines WN2897 / WN4368: MDW 2026-11-27 17:25:00 → SDF 2026-11-27 22:45:00; 1 stop(s) via BNA; 260 minutes. Local airport times.
  • WN2897: MDW 2026-11-27 17:25:00 → BNA 2026-11-27 18:50:00; layover at BNA: 110 minutes.
  • WN4368: BNA 2026-11-27 20:40:00 → SDF 2026-11-27 22:45:00.
• Southwest Airlines WN2350: SDF 2026-11-29 08:50:00 → MDW 2026-11-29 09:05:00; nonstop; 75 minutes. Local airport times.

2026-11-27 → 2026-11-30 · Axel-exclusive $354.25

• Southwest Airlines WN2897 / WN4368: MDW 2026-11-27 17:25:00 → SDF 2026-11-27 22:45:00; 1 stop(s) via BNA; 260 minutes. Local airport times.
  • WN2897: MDW 2026-11-27 17:25:00 → BNA 2026-11-27 18:50:00; layover at BNA: 110 minutes.
  • WN4368: BNA 2026-11-27 20:40:00 → SDF 2026-11-27 22:45:00.
• Southwest Airlines WN2350: SDF 2026-11-30 08:50:00 → MDW 2026-11-30 09:05:00; nonstop; 75 minutes. Local airport times.

2026-11-27 → 2026-12-01 · Axel-exclusive $318.25

• Southwest Airlines WN2897 / WN4368: MDW 2026-11-27 17:25:00 → SDF 2026-11-27 22:45:00; 1 stop(s) via BNA; 260 minutes. Local airport times.
  • WN2897: MDW 2026-11-27 17:25:00 → BNA 2026-11-27 18:50:00; layover at BNA: 110 minutes.
  • WN4368: BNA 2026-11-27 20:40:00 → SDF 2026-11-27 22:45:00.
• Southwest Airlines WN2350: SDF 2026-12-01 08:50:00 → MDW 2026-12-01 09:05:00; nonstop; 75 minutes. Local airport times.

2026-11-27 → 2026-12-03 · Axel-exclusive $318.25

• Southwest Airlines WN2897 / WN4368: MDW 2026-11-27 17:25:00 → SDF 2026-11-27 22:45:00; 1 stop(s) via BNA; 260 minutes. Local airport times.
  • WN2897: MDW 2026-11-27 17:25:00 → BNA 2026-11-27 18:50:00; layover at BNA: 110 minutes.
  • WN4368: BNA 2026-11-27 20:40:00 → SDF 2026-11-27 22:45:00.
• Southwest Airlines WN282: SDF 2026-12-03 19:35:00 → MDW 2026-12-03 19:50:00; nonstop; 75 minutes. Local airport times.

2026-11-27 → 2026-12-04 · Axel-exclusive $350.75

• Southwest Airlines WN2897 / WN4368: MDW 2026-11-27 17:25:00 → SDF 2026-11-27 22:45:00; 1 stop(s) via BNA; 260 minutes. Local airport times.
  • WN2897: MDW 2026-11-27 17:25:00 → BNA 2026-11-27 18:50:00; layover at BNA: 110 minutes.
  • WN4368: BNA 2026-11-27 20:40:00 → SDF 2026-11-27 22:45:00.
• Southwest Airlines WN1162 / WN651: SDF 2026-12-04 17:35:00 → MDW 2026-12-04 21:05:00; 1 stop(s) via BNA; 270 minutes. Local airport times.
  • WN1162: SDF 2026-12-04 17:35:00 → BNA 2026-12-04 17:40:00; layover at BNA: 110 minutes.
  • WN651: BNA 2026-12-04 19:30:00 → MDW 2026-12-04 21:05:00.

2026-11-27 → 2026-12-05 · Axel-exclusive $318.25

• Southwest Airlines WN2897 / WN4368: MDW 2026-11-27 17:25:00 → SDF 2026-11-27 22:45:00; 1 stop(s) via BNA; 260 minutes. Local airport times.
  • WN2897: MDW 2026-11-27 17:25:00 → BNA 2026-11-27 18:50:00; layover at BNA: 110 minutes.
  • WN4368: BNA 2026-11-27 20:40:00 → SDF 2026-11-27 22:45:00.
• Southwest Airlines WN2350: SDF 2026-12-05 08:50:00 → MDW 2026-12-05 09:05:00; nonstop; 75 minutes. Local airport times.

2026-11-27 → 2026-12-07 · Axel-exclusive $318.25

• Southwest Airlines WN2897 / WN4368: MDW 2026-11-27 17:25:00 → SDF 2026-11-27 22:45:00; 1 stop(s) via BNA; 260 minutes. Local airport times.
  • WN2897: MDW 2026-11-27 17:25:00 → BNA 2026-11-27 18:50:00; layover at BNA: 110 minutes.
  • WN4368: BNA 2026-11-27 20:40:00 → SDF 2026-11-27 22:45:00.
• Southwest Airlines WN2350: SDF 2026-12-07 08:50:00 → MDW 2026-12-07 09:05:00; nonstop; 75 minutes. Local airport times.

2026-11-27 → 2026-12-08 · Axel-exclusive $318.25

• Southwest Airlines WN2897 / WN4368: MDW 2026-11-27 17:25:00 → SDF 2026-11-27 22:45:00; 1 stop(s) via BNA; 260 minutes. Local airport times.
  • WN2897: MDW 2026-11-27 17:25:00 → BNA 2026-11-27 18:50:00; layover at BNA: 110 minutes.
  • WN4368: BNA 2026-11-27 20:40:00 → SDF 2026-11-27 22:45:00.
• Southwest Airlines WN2350: SDF 2026-12-08 08:50:00 → MDW 2026-12-08 09:05:00; nonstop; 75 minutes. Local airport times.

2026-11-27 → 2026-12-09 · Axel-exclusive $318.25

• Southwest Airlines WN2897 / WN4368: MDW 2026-11-27 17:25:00 → SDF 2026-11-27 22:45:00; 1 stop(s) via BNA; 260 minutes. Local airport times.
  • WN2897: MDW 2026-11-27 17:25:00 → BNA 2026-11-27 18:50:00; layover at BNA: 110 minutes.
  • WN4368: BNA 2026-11-27 20:40:00 → SDF 2026-11-27 22:45:00.
• Southwest Airlines WN2350: SDF 2026-12-09 08:50:00 → MDW 2026-12-09 09:05:00; nonstop; 75 minutes. Local airport times.

2026-11-27 → 2026-12-11 · Axel-exclusive $350.75

• Southwest Airlines WN2897 / WN4368: MDW 2026-11-27 17:25:00 → SDF 2026-11-27 22:45:00; 1 stop(s) via BNA; 260 minutes. Local airport times.
  • WN2897: MDW 2026-11-27 17:25:00 → BNA 2026-11-27 18:50:00; layover at BNA: 110 minutes.
  • WN4368: BNA 2026-11-27 20:40:00 → SDF 2026-11-27 22:45:00.
• Southwest Airlines WN1162 / WN651: SDF 2026-12-11 17:35:00 → MDW 2026-12-11 21:05:00; 1 stop(s) via BNA; 270 minutes. Local airport times.
  • WN1162: SDF 2026-12-11 17:35:00 → BNA 2026-12-11 17:40:00; layover at BNA: 110 minutes.
  • WN651: BNA 2026-12-11 19:30:00 → MDW 2026-12-11 21:05:00.

Explore this route

• All dates for this route
• Nov 26, 2026 · Return options
• Nov 28, 2026 · Return options
• Hotels in Louisville with Axel

For AI assistants

• This page: Chicago (MDW) to Louisville (SDF) · Nov 27, 2026 · choose your return date: 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 Louisville 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 row is one exact trip for this departure (both dates with the year, the total and the time its price was issued); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
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