Richmond (RIC) to Chicago (MDW), Dec 18–20, 2026, return Dec 25–27, 2026: from $370 round trip

Richmond (RIC) to Chicago (MDW), Dec 18–20, 2026, return Dec 25–27, 2026: from $370 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $370 round trip, Axel-exclusive, Southwest Airlines, 1 stop, 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 dates Airline Flights Times, duration, stops Total price Price issued (UTC)
2026-12-18 → 2026-12-27 Southwest Airlines WN4353 / WN4410 08:10:00→09:15:00 2h 05m nonstop · 19:00:00→22:00:00 2h 00m nonstop Axel-exclusive $379.50 2026-10-29T01:04:28Z
2026-12-18 → 2026-12-27 Delta Air Lines DL1460 + DL1063 / DL2417 + DL1263 05:23:00→10:00:00 5h 37m 1 stop via ATL · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $471.50 2026-10-29T01:04:28Z
2026-12-18 → 2026-12-25 Southwest Airlines WN4353 / WN909 08:10:00→09:15:00 2h 05m nonstop · 13:15:00→16:00:00 1h 45m nonstop Axel-exclusive $379.50 2026-10-29T01:04:28Z
2026-12-18 → 2026-12-26 Southwest Airlines WN4353 / WN1353 08:10:00→09:15:00 2h 05m nonstop · 12:45:00→15:35:00 1h 50m nonstop Axel-exclusive $379.50 2026-10-29T01:04:28Z
2026-12-19 → 2026-12-27 Southwest Airlines WN4353 / WN4410 08:10:00→09:15:00 2h 05m nonstop · 19:00:00→22:00:00 2h 00m nonstop Axel-exclusive $429.00 2026-10-29T01:04:28Z
2026-12-20 → 2026-12-27 Southwest Airlines WN2327 / WN4410 08:10:00→09:15:00 2h 05m nonstop · 19:00:00→22:00:00 2h 00m nonstop Axel-exclusive $429.00 2026-10-29T01:04:28Z
2026-12-19 → 2026-12-25 Southwest Airlines WN4353 / WN909 08:10:00→09:15:00 2h 05m nonstop · 13:15:00→16:00:00 1h 45m nonstop Axel-exclusive $429.00 2026-10-29T01:04:28Z
2026-12-20 → 2026-12-25 Southwest Airlines WN2327 / WN909 08:10:00→09:15:00 2h 05m nonstop · 13:15:00→16:00:00 1h 45m nonstop Axel-exclusive $429.00 2026-10-29T01:04:28Z
2026-12-20 → 2026-12-26 Southwest Airlines WN2327 / WN1353 08:10:00→09:15:00 2h 05m nonstop · 12:45:00→15:35:00 1h 50m nonstop Axel-exclusive $429.00 2026-10-29T01:04:28Z
2026-12-19 → 2026-12-26 Southwest Airlines WN4353 / WN1353 08:10:00→09:15:00 2h 05m nonstop · 12:45:00→15:35:00 1h 50m nonstop Axel-exclusive $429.00 2026-10-29T01:04:28Z
2026-12-18 → 2026-12-27 Southwest Airlines WN909 + WN1072 / WN4410 16:40:00→20:15:00 4h 35m 1 stop via BWI · 19:00:00→22:00:00 2h 00m nonstop Axel-exclusive $369.50 2026-10-29T01:04:28Z
2026-12-18 → 2026-12-26 Southwest Airlines WN382 + WN2062 / WN1353 12:15:00→16:15:00 5h 00m 1 stop via BNA · 12:45:00→15:35:00 1h 50m nonstop Axel-exclusive $369.50 2026-10-29T01:04:28Z
2026-12-18 → 2026-12-27 Southwest Airlines WN382 + WN2062 / WN4410 12:15:00→16:15:00 5h 00m 1 stop via BNA · 19:00:00→22:00:00 2h 00m nonstop Axel-exclusive $369.50 2026-10-29T01:04:28Z
2026-12-18 → 2026-12-25 Southwest Airlines WN909 + WN1072 / WN909 16:40:00→20:15:00 4h 35m 1 stop via BWI · 13:15:00→16:00:00 1h 45m nonstop Axel-exclusive $369.50 2026-10-29T01:04:28Z
2026-12-18 → 2026-12-26 Southwest Airlines WN909 + WN1072 / WN1353 16:40:00→20:15:00 4h 35m 1 stop via BWI · 12:45:00→15:35:00 1h 50m nonstop Axel-exclusive $369.50 2026-10-29T01:04:28Z
2026-12-18 → 2026-12-25 Southwest Airlines WN382 + WN2062 / WN909 12:15:00→16:15:00 5h 00m 1 stop via BNA · 13:15:00→16:00:00 1h 45m nonstop Axel-exclusive $369.50 2026-10-29T01:04:28Z
2026-12-20 → 2026-12-26 Southwest Airlines WN382 + WN2062 / WN1353 12:15:00→16:15:00 5h 00m 1 stop via BNA · 12:45:00→15:35:00 1h 50m nonstop Axel-exclusive $416.00 2026-10-29T01:04:28Z
2026-12-19 → 2026-12-25 Southwest Airlines WN909 + WN1072 / WN909 16:40:00→20:15:00 4h 35m 1 stop via BWI · 13:15:00→16:00:00 1h 45m nonstop Axel-exclusive $416.00 2026-10-29T01:04:28Z
2026-12-20 → 2026-12-27 Southwest Airlines WN382 + WN2062 / WN4410 12:15:00→16:15:00 5h 00m 1 stop via BNA · 19:00:00→22:00:00 2h 00m nonstop Axel-exclusive $416.00 2026-10-29T01:04:28Z
2026-12-19 → 2026-12-25 Southwest Airlines WN382 + WN2062 / WN909 12:15:00→16:15:00 5h 00m 1 stop via BNA · 13:15:00→16:00:00 1h 45m nonstop Axel-exclusive $416.00 2026-10-29T01:04:28Z
2026-12-19 → 2026-12-26 Southwest Airlines WN382 + WN2062 / WN1353 12:15:00→16:15:00 5h 00m 1 stop via BNA · 12:45:00→15:35:00 1h 50m nonstop Axel-exclusive $416.00 2026-10-29T01:04:28Z
2026-12-20 → 2026-12-25 Southwest Airlines WN382 + WN2062 / WN909 12:15:00→16:15:00 5h 00m 1 stop via BNA · 13:15:00→16:00:00 1h 45m nonstop Axel-exclusive $416.00 2026-10-29T01:04:28Z
2026-12-19 → 2026-12-27 Southwest Airlines WN382 + WN2062 / WN4410 12:15:00→16:15:00 5h 00m 1 stop via BNA · 19:00:00→22:00:00 2h 00m nonstop Axel-exclusive $416.00 2026-10-29T01:04:28Z
2026-12-20 → 2026-12-25 Southwest Airlines WN909 + WN1072 / WN909 16:40:00→20:15:00 4h 35m 1 stop via BWI · 13:15:00→16:00:00 1h 45m nonstop Axel-exclusive $416.00 2026-10-29T01:04:28Z
2026-12-20 → 2026-12-26 Southwest Airlines WN909 + WN1072 / WN1353 16:40:00→20:15:00 4h 35m 1 stop via BWI · 12:45:00→15:35:00 1h 50m nonstop Axel-exclusive $416.00 2026-10-29T01:04:28Z
2026-12-20 → 2026-12-27 Southwest Airlines WN909 + WN1072 / WN4410 16:40:00→20:15:00 4h 35m 1 stop via BWI · 19:00:00→22:00:00 2h 00m nonstop Axel-exclusive $416.00 2026-10-29T01:04:28Z
2026-12-19 → 2026-12-27 Southwest Airlines WN909 + WN1072 / WN4410 16:40:00→20:15:00 4h 35m 1 stop via BWI · 19:00:00→22:00:00 2h 00m nonstop Axel-exclusive $416.00 2026-10-29T01:04:28Z
2026-12-19 → 2026-12-26 Southwest Airlines WN909 + WN1072 / WN1353 16:40:00→20:15:00 4h 35m 1 stop via BWI · 12:45:00→15:35:00 1h 50m nonstop Axel-exclusive $416.00 2026-10-29T01:04:28Z
2026-12-18 → 2026-12-26 Delta Air Lines DL5055 + DL4677 / DL2417 + DL1263 12:59:00→18:01:00 6h 02m 1 stop via DTW · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $471.50 2026-10-29T01:04:28Z
2026-12-18 → 2026-12-26 Delta Air Lines DL1460 + DL1063 / DL2417 + DL1263 05:23:00→10:00:00 5h 37m 1 stop via ATL · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $471.50 2026-10-29T01:04:28Z
2026-12-18 → 2026-12-25 Delta Air Lines DL1460 + DL1063 / DL2417 + DL1263 05:23:00→10:00:00 5h 37m 1 stop via ATL · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $471.50 2026-10-29T01:04:28Z
2026-12-18 → 2026-12-27 Delta Air Lines DL5055 + DL4677 / DL2417 + DL1263 12:59:00→18:01:00 6h 02m 1 stop via DTW · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $471.50 2026-10-29T01:04:28Z
2026-12-18 → 2026-12-25 Delta Air Lines DL5055 + DL4677 / DL2417 + DL1263 12:59:00→18:01:00 6h 02m 1 stop via DTW · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $471.50 2026-10-29T01:04:28Z
2026-12-19 → 2026-12-26 Delta Air Lines DL5055 + DL4677 / DL2417 + DL1263 12:59:00→18:01:00 6h 02m 1 stop via DTW · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $533.00 2026-10-29T01:04:28Z
2026-12-20 → 2026-12-26 Delta Air Lines DL1460 + DL1063 / DL2417 + DL1263 05:23:00→10:00:00 5h 37m 1 stop via ATL · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $533.00 2026-10-29T01:04:28Z
2026-12-19 → 2026-12-26 Delta Air Lines DL1460 + DL1063 / DL2417 + DL1263 05:23:00→10:00:00 5h 37m 1 stop via ATL · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $533.00 2026-10-29T01:04:28Z
2026-12-20 → 2026-12-27 Delta Air Lines DL5055 + DL4677 / DL2417 + DL1263 12:59:00→18:01:00 6h 02m 1 stop via DTW · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $533.00 2026-10-29T01:04:28Z
2026-12-19 → 2026-12-25 Delta Air Lines DL5055 + DL4677 / DL2417 + DL1263 12:59:00→18:01:00 6h 02m 1 stop via DTW · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $533.00 2026-10-29T01:04:28Z
2026-12-19 → 2026-12-25 Delta Air Lines DL1460 + DL1063 / DL2417 + DL1263 05:23:00→10:00:00 5h 37m 1 stop via ATL · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $533.00 2026-10-29T01:04:28Z
2026-12-19 → 2026-12-27 Delta Air Lines DL1460 + DL1063 / DL2417 + DL1263 05:23:00→10:00:00 5h 37m 1 stop via ATL · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $533.00 2026-10-29T01:04:28Z
2026-12-19 → 2026-12-27 Delta Air Lines DL5055 + DL4677 / DL2417 + DL1263 12:59:00→18:01:00 6h 02m 1 stop via DTW · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $533.00 2026-10-29T01:04:28Z
2026-12-20 → 2026-12-26 Delta Air Lines DL5055 + DL4677 / DL2417 + DL1263 12:59:00→18:01:00 6h 02m 1 stop via DTW · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $533.00 2026-10-29T01:04:28Z
2026-12-20 → 2026-12-27 Delta Air Lines DL1460 + DL1063 / DL2417 + DL1263 05:23:00→10:00:00 5h 37m 1 stop via ATL · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $533.00 2026-10-29T01:04:28Z
2026-12-20 → 2026-12-25 Delta Air Lines DL5055 + DL4677 / DL2417 + DL1263 12:59:00→18:01:00 6h 02m 1 stop via DTW · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $533.00 2026-10-29T01:04:28Z
2026-12-20 → 2026-12-25 Delta Air Lines DL1460 + DL1063 / DL2417 + DL1263 05:23:00→10:00:00 5h 37m 1 stop via ATL · 13:02:00→20:33:00 6h 31m 1 stop via ATL Axel-exclusive $533.00 2026-10-29T01:04:28Z

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: Richmond to Chicago (MDW) flight deals

2026-12-18 → 2026-12-27 · Axel-exclusive $379.50

2026-12-18 → 2026-12-27 · Axel-exclusive $471.50

2026-12-18 → 2026-12-25 · Axel-exclusive $379.50

2026-12-18 → 2026-12-26 · Axel-exclusive $379.50

2026-12-19 → 2026-12-27 · Axel-exclusive $429.00

2026-12-20 → 2026-12-27 · Axel-exclusive $429.00

2026-12-19 → 2026-12-25 · Axel-exclusive $429.00

2026-12-20 → 2026-12-25 · Axel-exclusive $429.00

2026-12-20 → 2026-12-26 · Axel-exclusive $429.00

2026-12-19 → 2026-12-26 · Axel-exclusive $429.00

2026-12-18 → 2026-12-27 · Axel-exclusive $369.50

2026-12-18 → 2026-12-26 · Axel-exclusive $369.50

2026-12-18 → 2026-12-27 · Axel-exclusive $369.50

2026-12-18 → 2026-12-25 · Axel-exclusive $369.50

2026-12-18 → 2026-12-26 · Axel-exclusive $369.50

2026-12-18 → 2026-12-25 · Axel-exclusive $369.50

2026-12-20 → 2026-12-26 · Axel-exclusive $416.00

2026-12-19 → 2026-12-25 · Axel-exclusive $416.00

2026-12-20 → 2026-12-27 · Axel-exclusive $416.00

2026-12-19 → 2026-12-25 · Axel-exclusive $416.00

2026-12-19 → 2026-12-26 · Axel-exclusive $416.00

2026-12-20 → 2026-12-25 · Axel-exclusive $416.00

2026-12-19 → 2026-12-27 · Axel-exclusive $416.00

2026-12-20 → 2026-12-25 · Axel-exclusive $416.00

2026-12-20 → 2026-12-26 · Axel-exclusive $416.00

2026-12-20 → 2026-12-27 · Axel-exclusive $416.00

2026-12-19 → 2026-12-27 · Axel-exclusive $416.00

2026-12-19 → 2026-12-26 · Axel-exclusive $416.00

2026-12-18 → 2026-12-26 · Axel-exclusive $471.50

2026-12-18 → 2026-12-26 · Axel-exclusive $471.50

2026-12-18 → 2026-12-25 · Axel-exclusive $471.50

2026-12-18 → 2026-12-27 · Axel-exclusive $471.50

2026-12-18 → 2026-12-25 · Axel-exclusive $471.50

2026-12-19 → 2026-12-26 · Axel-exclusive $533.00

2026-12-20 → 2026-12-26 · Axel-exclusive $533.00

2026-12-19 → 2026-12-26 · Axel-exclusive $533.00

2026-12-20 → 2026-12-27 · Axel-exclusive $533.00

2026-12-19 → 2026-12-25 · Axel-exclusive $533.00

2026-12-19 → 2026-12-25 · Axel-exclusive $533.00

2026-12-19 → 2026-12-27 · Axel-exclusive $533.00

2026-12-19 → 2026-12-27 · Axel-exclusive $533.00

2026-12-20 → 2026-12-26 · Axel-exclusive $533.00

2026-12-20 → 2026-12-27 · Axel-exclusive $533.00

2026-12-20 → 2026-12-25 · Axel-exclusive $533.00

2026-12-20 → 2026-12-25 · Axel-exclusive $533.00

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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