Charleston (CHS) to Chicago (MDW), Nov 25, 2026: round trips from $334, one way from $209

Charleston (CHS) to Chicago (MDW), Nov 25, 2026: round trips from $334, one way from $209 on Axel, checked Oct 29, 2026. Lowest published fares: $334 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 25, 2026 – Dec 1, 2026; $209 one way, Axel-exclusive, Southwest Airlines, 1 stop, Nov 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.

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.

Exact travel dates Airline Flights Times, duration, stops Total price Price issued (UTC)
2026-11-25 · one way Southwest Airlines WN1959 + WN2062 11:00:00→16:15:00 6h 15m 1 stop via BNA Axel-exclusive $209.25 2026-10-29T00:55:53Z
2026-11-25 · one way Delta Air Lines DL5017 + DL4677 13:06:00→18:01:00 5h 55m 1 stop via DTW Axel-exclusive $236.25 2026-10-29T00:55:53Z
2026-11-25 → 2026-11-26 Southwest Airlines WN1959 + WN2062 / WN4116 11:00:00→16:15:00 6h 15m 1 stop via BNA · 20:35:00→23:40:00 2h 05m nonstop Axel-exclusive $381.38 2026-10-29T00:55:53Z
2026-11-25 → 2026-11-26 Delta Air Lines DL5017 + DL4677 / DL1063 + DL3179 13:06:00→18:01:00 5h 55m 1 stop via DTW · 11:28:00→17:54:00 5h 26m 1 stop via ATL Axel-exclusive $445.50 2026-10-29T00:55:53Z
2026-11-25 → 2026-11-27 Southwest Airlines WN1959 + WN2062 / WN2897 + WN746 11:00:00→16:15:00 6h 15m 1 stop via BNA · 17:25:00→00:15:00 5h 50m 1 stop via BNA Axel-exclusive $398.26 2026-10-29T00:55:53Z
2026-11-25 → 2026-11-27 Delta Air Lines DL5017 + DL4677 / DL1063 + DL3179 13:06:00→18:01:00 5h 55m 1 stop via DTW · 11:28:00→17:54:00 5h 26m 1 stop via ATL Axel-exclusive $445.50 2026-10-29T00:55:53Z
2026-11-25 → 2026-11-28 Southwest Airlines WN1959 + WN2062 / WN988 11:00:00→16:15:00 6h 15m 1 stop via BNA · 13:00:00→16:05:00 2h 05m nonstop Axel-exclusive $381.38 2026-10-29T00:55:53Z
2026-11-25 → 2026-11-28 Delta Air Lines DL5017 + DL4677 / DL1063 + DL3179 13:06:00→18:01:00 5h 55m 1 stop via DTW · 11:28:00→17:54:00 5h 26m 1 stop via ATL Axel-exclusive $445.50 2026-10-29T00:55:53Z
2026-11-25 → 2026-11-29 Southwest Airlines WN1959 + WN2062 / WN4116 11:00:00→16:15:00 6h 15m 1 stop via BNA · 20:35:00→23:40:00 2h 05m nonstop Axel-exclusive $381.38 2026-10-29T00:55:53Z
2026-11-25 → 2026-11-29 Delta Air Lines DL5017 + DL4677 / DL1063 + DL3179 13:06:00→18:01:00 5h 55m 1 stop via DTW · 11:28:00→17:54:00 5h 26m 1 stop via ATL Axel-exclusive $445.50 2026-10-29T00:55:53Z
2026-11-25 → 2026-11-30 Southwest Airlines WN1959 + WN2062 / WN4336 11:00:00→16:15:00 6h 15m 1 stop via BNA · 13:25:00→16:30:00 2h 05m nonstop Axel-exclusive $381.38 2026-10-29T00:55:53Z
2026-11-25 → 2026-11-30 Delta Air Lines DL5017 + DL4677 / DL1063 + DL3179 13:06:00→18:01:00 5h 55m 1 stop via DTW · 11:28:00→17:54:00 5h 26m 1 stop via ATL Axel-exclusive $445.50 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-01 Southwest Airlines WN1959 + WN2062 / WN4336 11:00:00→16:15:00 6h 15m 1 stop via BNA · 13:25:00→16:30:00 2h 05m nonstop Axel-exclusive $334.13 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-01 Delta Air Lines DL5017 + DL4677 / DL1063 + DL3179 13:06:00→18:01:00 5h 55m 1 stop via DTW · 11:28:00→17:54:00 5h 26m 1 stop via ATL Axel-exclusive $387.75 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-02 Southwest Airlines WN1959 + WN2062 / WN4336 11:00:00→16:15:00 6h 15m 1 stop via BNA · 13:25:00→16:30:00 2h 05m nonstop Axel-exclusive $334.13 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-02 Delta Air Lines DL5017 + DL4677 / DL1063 + DL3179 13:06:00→18:01:00 5h 55m 1 stop via DTW · 11:28:00→17:54:00 5h 26m 1 stop via ATL Axel-exclusive $387.75 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-03 Southwest Airlines WN1959 + WN2062 / WN4116 11:00:00→16:15:00 6h 15m 1 stop via BNA · 20:35:00→23:40:00 2h 05m nonstop Axel-exclusive $334.13 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-03 Delta Air Lines DL5017 + DL4677 / DL1063 + DL3179 13:06:00→18:01:00 5h 55m 1 stop via DTW · 11:28:00→17:54:00 5h 26m 1 stop via ATL Axel-exclusive $387.75 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-04 Southwest Airlines WN1959 + WN2062 / WN2897 + WN746 11:00:00→16:15:00 6h 15m 1 stop via BNA · 17:25:00→00:15:00 5h 50m 1 stop via BNA Axel-exclusive $346.63 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-04 Delta Air Lines DL5017 + DL4677 / DL1063 + DL3179 13:06:00→18:01:00 5h 55m 1 stop via DTW · 11:28:00→17:54:00 5h 26m 1 stop via ATL Axel-exclusive $387.75 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-05 Southwest Airlines WN1959 + WN2062 / WN988 11:00:00→16:15:00 6h 15m 1 stop via BNA · 13:00:00→16:05:00 2h 05m nonstop Axel-exclusive $334.13 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-05 Delta Air Lines DL5017 + DL4677 / DL1063 + DL3179 13:06:00→18:01:00 5h 55m 1 stop via DTW · 11:28:00→17:54:00 5h 26m 1 stop via ATL Axel-exclusive $387.75 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-06 Southwest Airlines WN1959 + WN2062 / WN4116 11:00:00→16:15:00 6h 15m 1 stop via BNA · 20:35:00→23:40:00 2h 05m nonstop Axel-exclusive $334.13 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-06 Delta Air Lines DL5017 + DL4677 / DL1063 + DL3179 13:06:00→18:01:00 5h 55m 1 stop via DTW · 11:28:00→17:54:00 5h 26m 1 stop via ATL Axel-exclusive $387.75 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-07 Southwest Airlines WN1959 + WN2062 / WN4336 11:00:00→16:15:00 6h 15m 1 stop via BNA · 13:25:00→16:30:00 2h 05m nonstop Axel-exclusive $334.13 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-07 Delta Air Lines DL5017 + DL4677 / DL1063 + DL3179 13:06:00→18:01:00 5h 55m 1 stop via DTW · 11:28:00→17:54:00 5h 26m 1 stop via ATL Axel-exclusive $387.75 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-08 Southwest Airlines WN1959 + WN2062 / WN4336 11:00:00→16:15:00 6h 15m 1 stop via BNA · 13:25:00→16:30:00 2h 05m nonstop Axel-exclusive $334.13 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-08 Delta Air Lines DL5017 + DL4677 / DL1063 + DL3179 13:06:00→18:01:00 5h 55m 1 stop via DTW · 11:28:00→17:54:00 5h 26m 1 stop via ATL Axel-exclusive $387.75 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-09 Southwest Airlines WN1959 + WN2062 / WN4336 11:00:00→16:15:00 6h 15m 1 stop via BNA · 13:25:00→16:30:00 2h 05m nonstop Axel-exclusive $334.13 2026-10-29T00:55:53Z
2026-11-25 → 2026-12-09 Delta Air Lines DL5017 + DL4677 / DL1063 + DL3179 13:06:00→18:01:00 5h 55m 1 stop via DTW · 11:28:00→17:54:00 5h 26m 1 stop via ATL Axel-exclusive $387.75 2026-10-29T00:55:53Z

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: Charleston to Chicago (MDW) flight deals

2026-11-25 · one way · Axel-exclusive $209.25

2026-11-25 · one way · Axel-exclusive $236.25

2026-11-25 → 2026-11-26 · Axel-exclusive $381.38

2026-11-25 → 2026-11-26 · Axel-exclusive $445.50

2026-11-25 → 2026-11-27 · Axel-exclusive $398.26

2026-11-25 → 2026-11-27 · Axel-exclusive $445.50

2026-11-25 → 2026-11-28 · Axel-exclusive $381.38

2026-11-25 → 2026-11-28 · Axel-exclusive $445.50

2026-11-25 → 2026-11-29 · Axel-exclusive $381.38

2026-11-25 → 2026-11-29 · Axel-exclusive $445.50

2026-11-25 → 2026-12-01 · Axel-exclusive $334.13

2026-11-25 → 2026-12-01 · Axel-exclusive $387.75

2026-11-25 → 2026-12-02 · Axel-exclusive $334.13

2026-11-25 → 2026-12-02 · Axel-exclusive $387.75

2026-11-25 → 2026-12-03 · Axel-exclusive $334.13

2026-11-25 → 2026-12-03 · Axel-exclusive $387.75

2026-11-25 → 2026-12-05 · Axel-exclusive $334.13

2026-11-25 → 2026-12-05 · Axel-exclusive $387.75

2026-11-25 → 2026-12-06 · Axel-exclusive $334.13

2026-11-25 → 2026-12-06 · Axel-exclusive $387.75

2026-11-25 → 2026-12-07 · Axel-exclusive $334.13

2026-11-25 → 2026-12-07 · Axel-exclusive $387.75

2026-11-25 → 2026-12-09 · Axel-exclusive $334.13

2026-11-25 → 2026-12-09 · Axel-exclusive $387.75

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