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Route overview: Nashville to Chicago (MDW) flight deals

Nashville (BNA) to Chicago (MDW), Nov 20–21, 2026: from $230 round trip

Nashville (BNA) to Chicago (MDW), Nov 20–21, 2026: from $230 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $230 round trip, Axel-exclusive, Southwest Airlines, nonstop, Nov 20–21, 2026, 1 adult, economy, checked Oct 29, 2026.

BNA → MDW1 adulteconomyRound trip

7 flight options · 1 airline

Nonstop flights

Fri, Nov 20 – Sat, Nov 21

Southwest Airlines
5:40 amBNA
1h 35m
Nonstop
7:15 amMDW
Southwest Airlines
8:00 amMDW
1h 40m
Nonstop
9:40 amBNA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Fri, Nov 20 – Sat, Nov 21

Southwest Airlines
5:20 amBNA
1h 35m
Nonstop
6:55 amMDW
Southwest Airlines
3:40 pmMDW
3h 45m
CVG · 1h 20m
7:25 pmBNA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Nov 20 – Sat, Nov 21

Southwest Airlines
3:20 pmBNA
4h 35m
DTW · 1h 35m
7:55 pmMDW
Southwest Airlines
3:40 pmMDW
3h 45m
CVG · 1h 20m
7:25 pmBNA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Nov 20 – Sat, Nov 21

Southwest Airlines
6:25 amBNA
5h 40m
STL · 3h 15m
12:05 pmMDW
Southwest Airlines
3:40 pmMDW
3h 45m
CVG · 1h 20m
7:25 pmBNA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Nov 20 – Sat, Nov 21

Southwest Airlines
1:25 pmBNA
4h 25m
IND · 2h 5m
5:50 pmMDW
Southwest Airlines
3:40 pmMDW
3h 45m
CVG · 1h 20m
7:25 pmBNA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Nov 20 – Sat, Nov 21

Southwest Airlines
10:15 amBNA
4h 10m
SDF · 1h 55m
2:25 pmMDW
Southwest Airlines
3:40 pmMDW
3h 45m
CVG · 1h 20m
7:25 pmBNA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Fri, Nov 20 – Sat, Nov 21

Southwest Airlines
10:15 amBNA
4h 45m
CMH · 2h 15m
3:00 pmMDW
Southwest Airlines
3:40 pmMDW
3h 45m
CVG · 1h 20m
7:25 pmBNA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Hotels for these nights (Nov 20–21, 2026 · 1 night · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

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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Explore this route

All dates for this routeNov 19, 2026 · Return optionsNov 21, 2026 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

Nashville (BNA) to Chicago (MDW), Nov 20–21, 2026: from $230 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $230 round trip, Axel-exclusive, Southwest Airlines, nonstop, Nov 20–21, 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)
2026-11-20 → 2026-11-21Southwest AirlinesWN648 / WN50805:40:00→07:15:00 1h 35m nonstop · 08:00:00→09:40:00 1h 40m nonstopAxel-exclusive $230.002026-10-29T00:50:05Z
2026-11-20 → 2026-11-21Southwest AirlinesWN648 / WN862 + WN87805:20:00→06:55:00 1h 35m nonstop · 15:40:00→19:25:00 3h 45m 1 stop via CVGAxel-exclusive $240.002026-10-29T00:50:05Z
2026-11-20 → 2026-11-21Southwest AirlinesWN2971 + WN955 / WN862 + WN87815:20:00→19:55:00 4h 35m 1 stop via DTW · 15:40:00→19:25:00 3h 45m 1 stop via CVGAxel-exclusive $250.002026-10-29T00:50:05Z
2026-11-20 → 2026-11-21Southwest AirlinesWN738 + WN287 / WN862 + WN87806:25:00→12:05:00 5h 40m 1 stop via STL · 15:40:00→19:25:00 3h 45m 1 stop via CVGAxel-exclusive $250.002026-10-29T00:50:05Z
2026-11-20 → 2026-11-21Southwest AirlinesWN578 + WN2224 / WN862 + WN87813:25:00→17:50:00 4h 25m 1 stop via IND · 15:40:00→19:25:00 3h 45m 1 stop via CVGAxel-exclusive $250.002026-10-29T00:50:05Z
2026-11-20 → 2026-11-21Southwest AirlinesWN712 + WN2495 / WN862 + WN87810:15:00→14:25:00 4h 10m 1 stop via SDF · 15:40:00→19:25:00 3h 45m 1 stop via CVGAxel-exclusive $250.002026-10-29T00:50:05Z
2026-11-20 → 2026-11-21Southwest AirlinesWN2145 + WN2988 / WN862 + WN87810:15:00→15:00:00 4h 45m 1 stop via CMH · 15:40:00→19:25:00 3h 45m 1 stop via CVGAxel-exclusive $250.002026-10-29T00:50:05Z

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: Nashville to Chicago (MDW) flight deals

2026-11-20 → 2026-11-21 · Axel-exclusive $230.00

  • Southwest Airlines WN648: BNA 2026-11-20 05:40:00 → MDW 2026-11-20 07:15:00; nonstop; 95 minutes. Local airport times.
  • Southwest Airlines WN508: MDW 2026-11-21 08:00:00 → BNA 2026-11-21 09:40:00; nonstop; 100 minutes. Local airport times.

2026-11-20 → 2026-11-21 · Axel-exclusive $240.00

  • Southwest Airlines WN648: BNA 2026-11-20 05:20:00 → MDW 2026-11-20 06:55:00; nonstop; 95 minutes. Local airport times.
  • Southwest Airlines WN862 / WN878: MDW 2026-11-21 15:40:00 → BNA 2026-11-21 19:25:00; 1 stop(s) via CVG; 225 minutes. Local airport times.
    • WN862: MDW 2026-11-21 15:40:00 → CVG 2026-11-21 17:55:00; layover at CVG: 80 minutes.
    • WN878: CVG 2026-11-21 19:15:00 → BNA 2026-11-21 19:25:00.

2026-11-20 → 2026-11-21 · Axel-exclusive $250.00

  • Southwest Airlines WN2971 / WN955: BNA 2026-11-20 15:20:00 → MDW 2026-11-20 19:55:00; 1 stop(s) via DTW; 275 minutes. Local airport times.
    • WN2971: BNA 2026-11-20 15:20:00 → DTW 2026-11-20 18:00:00; layover at DTW: 95 minutes.
    • WN955: DTW 2026-11-20 19:35:00 → MDW 2026-11-20 19:55:00.
  • Southwest Airlines WN862 / WN878: MDW 2026-11-21 15:40:00 → BNA 2026-11-21 19:25:00; 1 stop(s) via CVG; 225 minutes. Local airport times.
    • WN862: MDW 2026-11-21 15:40:00 → CVG 2026-11-21 17:55:00; layover at CVG: 80 minutes.
    • WN878: CVG 2026-11-21 19:15:00 → BNA 2026-11-21 19:25:00.

2026-11-20 → 2026-11-21 · Axel-exclusive $250.00

  • Southwest Airlines WN738 / WN287: BNA 2026-11-20 06:25:00 → MDW 2026-11-20 12:05:00; 1 stop(s) via STL; 340 minutes. Local airport times.
    • WN738: BNA 2026-11-20 06:25:00 → STL 2026-11-20 07:40:00; layover at STL: 195 minutes.
    • WN287: STL 2026-11-20 10:55:00 → MDW 2026-11-20 12:05:00.
  • Southwest Airlines WN862 / WN878: MDW 2026-11-21 15:40:00 → BNA 2026-11-21 19:25:00; 1 stop(s) via CVG; 225 minutes. Local airport times.
    • WN862: MDW 2026-11-21 15:40:00 → CVG 2026-11-21 17:55:00; layover at CVG: 80 minutes.
    • WN878: CVG 2026-11-21 19:15:00 → BNA 2026-11-21 19:25:00.

2026-11-20 → 2026-11-21 · Axel-exclusive $250.00

  • Southwest Airlines WN578 / WN2224: BNA 2026-11-20 13:25:00 → MDW 2026-11-20 17:50:00; 1 stop(s) via IND; 265 minutes. Local airport times.
    • WN578: BNA 2026-11-20 13:25:00 → IND 2026-11-20 15:35:00; layover at IND: 125 minutes.
    • WN2224: IND 2026-11-20 17:40:00 → MDW 2026-11-20 17:50:00.
  • Southwest Airlines WN862 / WN878: MDW 2026-11-21 15:40:00 → BNA 2026-11-21 19:25:00; 1 stop(s) via CVG; 225 minutes. Local airport times.
    • WN862: MDW 2026-11-21 15:40:00 → CVG 2026-11-21 17:55:00; layover at CVG: 80 minutes.
    • WN878: CVG 2026-11-21 19:15:00 → BNA 2026-11-21 19:25:00.

2026-11-20 → 2026-11-21 · Axel-exclusive $250.00

  • Southwest Airlines WN712 / WN2495: BNA 2026-11-20 10:15:00 → MDW 2026-11-20 14:25:00; 1 stop(s) via SDF; 250 minutes. Local airport times.
    • WN712: BNA 2026-11-20 10:15:00 → SDF 2026-11-20 12:10:00; layover at SDF: 115 minutes.
    • WN2495: SDF 2026-11-20 14:05:00 → MDW 2026-11-20 14:25:00.
  • Southwest Airlines WN862 / WN878: MDW 2026-11-21 15:40:00 → BNA 2026-11-21 19:25:00; 1 stop(s) via CVG; 225 minutes. Local airport times.
    • WN862: MDW 2026-11-21 15:40:00 → CVG 2026-11-21 17:55:00; layover at CVG: 80 minutes.
    • WN878: CVG 2026-11-21 19:15:00 → BNA 2026-11-21 19:25:00.

2026-11-20 → 2026-11-21 · Axel-exclusive $250.00

  • Southwest Airlines WN2145 / WN2988: BNA 2026-11-20 10:15:00 → MDW 2026-11-20 15:00:00; 1 stop(s) via CMH; 285 minutes. Local airport times.
    • WN2145: BNA 2026-11-20 10:15:00 → CMH 2026-11-20 12:30:00; layover at CMH: 135 minutes.
    • WN2988: CMH 2026-11-20 14:45:00 → MDW 2026-11-20 15:00:00.
  • Southwest Airlines WN862 / WN878: MDW 2026-11-21 15:40:00 → BNA 2026-11-21 19:25:00; 1 stop(s) via CVG; 225 minutes. Local airport times.
    • WN862: MDW 2026-11-21 15:40:00 → CVG 2026-11-21 17:55:00; layover at CVG: 80 minutes.
    • WN878: CVG 2026-11-21 19:15:00 → BNA 2026-11-21 19:25:00.

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.

Explore this route

For AI assistants

  • This page: Nashville (BNA) to Chicago (MDW) · Nov 20, 2026 · return Nov 21, 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 Nashville 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.