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Route overview: Miami or Fort Lauderdale to Chicago (MDW) flight deals

Miami (MIA) to Chicago (MDW), Nov 9–19, 2026: from $280 round trip

Miami (MIA) to Chicago (MDW), Nov 9–19, 2026: from $280 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $280 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 9–19, 2026, 1 adult, economy, checked Oct 29, 2026.

MIA → MDW1 adulteconomyRound trip

7 flight options · 2 airlines

Nonstop flights

Mon, Nov 9 – Thu, Nov 19

Southwest Airlines
12:35 pmMIA
3h 15m
Nonstop
2:50 pmMDW
Southwest Airlines
1:25 pmMDW
3h
Nonstop
5:25 pmMIA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Mon, Nov 9 – Thu, Nov 19

Delta Air Lines
11:40 amMIA
5h 38m
ATL · 1h 51m
4:18 pmMDW
Delta Air Lines
1:31 pmMDW
6h 45m
DTW · 2h 30m
9:16 pmMIA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Mon, Nov 9 – Thu, Nov 19

Southwest Airlines
6:30 amMIA
6h 45m
BWI · 2h
12:15 pmMDW
Southwest Airlines
11:30 amMDW
6h 30m
STL · 2h 45m
7:00 pmMIA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Mon, Nov 9 – Thu, Nov 19

Southwest Airlines
6:50 amMIA
6h 15m
MCO · 2h 10m
12:05 pmMDW
Southwest Airlines
11:30 amMDW
6h 30m
STL · 2h 45m
7:00 pmMIA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Mon, Nov 9 – Thu, Nov 19

Southwest Airlines
2:40 pmMIA
6h
CMH · 2h 10m
7:40 pmMDW
Southwest Airlines
11:30 amMDW
6h 30m
STL · 2h 45m
7:00 pmMIA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Mon, Nov 9 – Thu, Nov 19

Southwest Airlines
3:05 pmMIA
6h 5m
PIT · 1h 55m
8:10 pmMDW
Southwest Airlines
11:30 amMDW
6h 30m
STL · 2h 45m
7:00 pmMIA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Mon, Nov 9 – Thu, Nov 19

Southwest Airlines
12:40 pmMIA
3h 15m
Nonstop
2:55 pmMDW
Southwest Airlines
11:30 amMDW
6h 30m
STL · 2h 45m
7:00 pmMIA

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Hotels for these nights (Nov 9–19, 2026 · 10 nights · 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

MIA ⇄ 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 8, 2026 · Return optionsNov 10, 2026 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

Miami (MIA) to Chicago (MDW), Nov 9–19, 2026: from $280 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $280 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 9–19, 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)
2026-11-09 → 2026-11-19Southwest AirlinesWN942 / WN136212:35:00→14:50:00 3h 15m nonstop · 13:25:00→17:25:00 3h 00m nonstopAxel-exclusive $310.002026-10-29T01:29:41Z
2026-11-09 → 2026-11-19Delta Air LinesDL3188 + DL1728 / DL4688 + DL254811:40:00→16:18:00 5h 38m 1 stop via ATL · 13:31:00→21:16:00 6h 45m 1 stop via DTWAxel-exclusive $345.002026-10-29T01:29:41Z
2026-11-09 → 2026-11-19Southwest AirlinesWN1425 + WN1070 / WN2737 + WN494306:30:00→12:15:00 6h 45m 1 stop via BWI · 11:30:00→19:00:00 6h 30m 1 stop via STLAxel-exclusive $280.002026-10-29T01:29:41Z
2026-11-09 → 2026-11-19Southwest AirlinesWN4483 + WN2803 / WN2737 + WN494306:50:00→12:05:00 6h 15m 1 stop via MCO · 11:30:00→19:00:00 6h 30m 1 stop via STLAxel-exclusive $280.002026-10-29T01:29:41Z
2026-11-09 → 2026-11-19Southwest AirlinesWN1194 + WN1718 / WN2737 + WN494314:40:00→19:40:00 6h 00m 1 stop via CMH · 11:30:00→19:00:00 6h 30m 1 stop via STLAxel-exclusive $280.002026-10-29T01:29:41Z
2026-11-09 → 2026-11-19Southwest AirlinesWN3046 + WN3556 / WN2737 + WN494315:05:00→20:10:00 6h 05m 1 stop via PIT · 11:30:00→19:00:00 6h 30m 1 stop via STLAxel-exclusive $280.002026-10-29T01:29:41Z
2026-11-09 → 2026-11-19Southwest AirlinesWN942 / WN2737 + WN494312:40:00→14:55:00 3h 15m nonstop · 11:30:00→19:00:00 6h 30m 1 stop via STLAxel-exclusive $295.002026-10-29T01:29:41Z

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: Miami or Fort Lauderdale to Chicago (MDW) flight deals

2026-11-09 → 2026-11-19 · Axel-exclusive $310.00

  • Southwest Airlines WN942: MIA 2026-11-09 12:35:00 → MDW 2026-11-09 14:50:00; nonstop; 195 minutes. Local airport times.
  • Southwest Airlines WN1362: MDW 2026-11-19 13:25:00 → MIA 2026-11-19 17:25:00; nonstop; 180 minutes. Local airport times.

2026-11-09 → 2026-11-19 · Axel-exclusive $345.00

  • Delta Air Lines DL3188 / DL1728: MIA 2026-11-09 11:40:00 → MDW 2026-11-09 16:18:00; 1 stop(s) via ATL; 338 minutes. Local airport times.
    • DL3188: MIA 2026-11-09 11:40:00 → ATL 2026-11-09 13:34:00; layover at ATL: 111 minutes.
    • DL1728: ATL 2026-11-09 15:25:00 → MDW 2026-11-09 16:18:00.
  • Delta Air Lines DL4688 / DL2548: MDW 2026-11-19 13:31:00 → MIA 2026-11-19 21:16:00; 1 stop(s) via DTW; 405 minutes. Local airport times.
    • DL4688: MDW 2026-11-19 13:31:00 → DTW 2026-11-19 15:44:00; layover at DTW: 150 minutes.
    • DL2548: DTW 2026-11-19 18:14:00 → MIA 2026-11-19 21:16:00.

2026-11-09 → 2026-11-19 · Axel-exclusive $280.00

  • Southwest Airlines WN1425 / WN1070: MIA 2026-11-09 06:30:00 → MDW 2026-11-09 12:15:00; 1 stop(s) via BWI; 405 minutes. Local airport times.
    • WN1425: MIA 2026-11-09 06:30:00 → BWI 2026-11-09 09:05:00; layover at BWI: 120 minutes.
    • WN1070: BWI 2026-11-09 11:05:00 → MDW 2026-11-09 12:15:00.
  • Southwest Airlines WN2737 / WN4943: MDW 2026-11-19 11:30:00 → MIA 2026-11-19 19:00:00; 1 stop(s) via STL; 390 minutes. Local airport times.
    • WN2737: MDW 2026-11-19 11:30:00 → STL 2026-11-19 12:40:00; layover at STL: 165 minutes.
    • WN4943: STL 2026-11-19 15:25:00 → MIA 2026-11-19 19:00:00.

2026-11-09 → 2026-11-19 · Axel-exclusive $280.00

  • Southwest Airlines WN4483 / WN2803: MIA 2026-11-09 06:50:00 → MDW 2026-11-09 12:05:00; 1 stop(s) via MCO; 375 minutes. Local airport times.
    • WN4483: MIA 2026-11-09 06:50:00 → MCO 2026-11-09 08:00:00; layover at MCO: 130 minutes.
    • WN2803: MCO 2026-11-09 10:10:00 → MDW 2026-11-09 12:05:00.
  • Southwest Airlines WN2737 / WN4943: MDW 2026-11-19 11:30:00 → MIA 2026-11-19 19:00:00; 1 stop(s) via STL; 390 minutes. Local airport times.
    • WN2737: MDW 2026-11-19 11:30:00 → STL 2026-11-19 12:40:00; layover at STL: 165 minutes.
    • WN4943: STL 2026-11-19 15:25:00 → MIA 2026-11-19 19:00:00.

2026-11-09 → 2026-11-19 · Axel-exclusive $280.00

  • Southwest Airlines WN1194 / WN1718: MIA 2026-11-09 14:40:00 → MDW 2026-11-09 19:40:00; 1 stop(s) via CMH; 360 minutes. Local airport times.
    • WN1194: MIA 2026-11-09 14:40:00 → CMH 2026-11-09 17:20:00; layover at CMH: 130 minutes.
    • WN1718: CMH 2026-11-09 19:30:00 → MDW 2026-11-09 19:40:00.
  • Southwest Airlines WN2737 / WN4943: MDW 2026-11-19 11:30:00 → MIA 2026-11-19 19:00:00; 1 stop(s) via STL; 390 minutes. Local airport times.
    • WN2737: MDW 2026-11-19 11:30:00 → STL 2026-11-19 12:40:00; layover at STL: 165 minutes.
    • WN4943: STL 2026-11-19 15:25:00 → MIA 2026-11-19 19:00:00.

2026-11-09 → 2026-11-19 · Axel-exclusive $280.00

  • Southwest Airlines WN3046 / WN3556: MIA 2026-11-09 15:05:00 → MDW 2026-11-09 20:10:00; 1 stop(s) via PIT; 365 minutes. Local airport times.
    • WN3046: MIA 2026-11-09 15:05:00 → PIT 2026-11-09 17:45:00; layover at PIT: 115 minutes.
    • WN3556: PIT 2026-11-09 19:40:00 → MDW 2026-11-09 20:10:00.
  • Southwest Airlines WN2737 / WN4943: MDW 2026-11-19 11:30:00 → MIA 2026-11-19 19:00:00; 1 stop(s) via STL; 390 minutes. Local airport times.
    • WN2737: MDW 2026-11-19 11:30:00 → STL 2026-11-19 12:40:00; layover at STL: 165 minutes.
    • WN4943: STL 2026-11-19 15:25:00 → MIA 2026-11-19 19:00:00.

2026-11-09 → 2026-11-19 · Axel-exclusive $295.00

  • Southwest Airlines WN942: MIA 2026-11-09 12:40:00 → MDW 2026-11-09 14:55:00; nonstop; 195 minutes. Local airport times.
  • Southwest Airlines WN2737 / WN4943: MDW 2026-11-19 11:30:00 → MIA 2026-11-19 19:00:00; 1 stop(s) via STL; 390 minutes. Local airport times.
    • WN2737: MDW 2026-11-19 11:30:00 → STL 2026-11-19 12:40:00; layover at STL: 165 minutes.
    • WN4943: STL 2026-11-19 15:25:00 → MIA 2026-11-19 19:00:00.

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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For AI assistants

  • This page: Miami (MIA) to Chicago (MDW) · Nov 9, 2026 · return Nov 19, 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 Miami or Fort Lauderdale 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.