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Route overview: Chicago to Miami (MIA) flight deals

Chicago → Miami

Jun 23, 2027 · return Jun 26, 2027

MDW → MIA1 adulteconomyRound trip

8 flight options · 2 airlines

Nonstop flights

Wed, Jun 23 – Sat, Jun 26

Southwest Airlines
12:55 pmMDW
3h
Nonstop
4:55 pmMIA
Southwest Airlines
3:00 pmMIA
3h 10m
Nonstop
5:10 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Jun 23 – Sat, Jun 26

Southwest Airlines
7:40 amMDW
3h
Nonstop
11:40 amMIA
Southwest Airlines
3:00 pmMIA
3h 10m
Nonstop
5:10 pmMDW

Round-trip total · 1 adult · Taxes included

One-stop flights

Wed, Jun 23 – Sat, Jun 26

Delta Air Lines
1:31 pmMDW
6h 45m
DTW · 2h 30m
9:16 pmMIA
Delta Air Lines
8:05 amMIA
5h 56m
DTW · 1h 34m
1:01 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Jun 23 – Sat, Jun 26

Southwest Airlines
7:40 amMDW
6h 25m
PIT · 2h 25m
3:05 pmMIA
Southwest Airlines
3:00 pmMIA
3h 10m
Nonstop
5:10 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Jun 23 – Sat, Jun 26

Southwest Airlines
5:25 pmMDW
5h 25m
BNA · 1h 40m
11:50 pmMIA
Southwest Airlines
3:00 pmMIA
3h 10m
Nonstop
5:10 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Jun 23 – Sat, Jun 26

Southwest Airlines
7:35 amMDW
6h
MCI · 1h 30m
2:35 pmMIA
Southwest Airlines
3:00 pmMIA
3h 10m
Nonstop
5:10 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Jun 23 – Sat, Jun 26

Southwest Airlines
4:25 pmMDW
4h 50m
MCO · 1h
10:15 pmMIA
Southwest Airlines
3:00 pmMIA
3h 10m
Nonstop
5:10 pmMDW

Round-trip total · 1 adult · Taxes included

Wed, Jun 23 – Sat, Jun 26

Southwest Airlines
11:30 amMDW
6h 30m
STL · 2h 45m
7:00 pmMIA
Southwest Airlines
3:00 pmMIA
3h 10m
Nonstop
5:10 pmMDW

Round-trip total · 1 adult · Taxes included

Make this trip yours

MDW ⇄ MIA

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 routeJun 22, 2027 → Jun 25, 2027Jun 24, 2027 → Jun 27, 2027Hotels in Miami with Axel
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Live price for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.

Route overview: Chicago to Miami (MIA) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-06-23 → 2027-06-26Southwest AirlinesWN1399 / WN2466$260.002026-10-29T01:29:10Z
2027-06-23 → 2027-06-26Delta Air LinesDL4688 + DL2548 / DL2638 + DL4688$295.002026-10-29T01:29:10Z
2027-06-23 → 2027-06-26Southwest AirlinesWN2383 / WN2466$260.002026-10-29T01:29:10Z
2027-06-23 → 2027-06-26Southwest AirlinesWN3002 + WN301 / WN2466$252.502026-10-29T01:29:10Z
2027-06-23 → 2027-06-26Southwest AirlinesWN2897 + WN4284 / WN2466$252.502026-10-29T01:29:10Z
2027-06-23 → 2027-06-26Southwest AirlinesWN2959 + WN833 / WN2466$252.502026-10-29T01:29:10Z
2027-06-23 → 2027-06-26Southwest AirlinesWN1908 + WN2643 / WN2466$252.502026-10-29T01:29:10Z
2027-06-23 → 2027-06-26Southwest AirlinesWN2737 + WN4943 / WN2466$252.502026-10-29T01:29:10Z

2027-06-23 → 2027-06-26 · $260.00

  • Southwest Airlines WN1399: MDW 2027-06-23 12:55:00 → MIA 2027-06-23 16:55:00; nonstop; 180 minutes. Local airport times.
  • Southwest Airlines WN2466: MIA 2027-06-26 15:00:00 → MDW 2027-06-26 17:10:00; nonstop; 190 minutes. Local airport times.

2027-06-23 → 2027-06-26 · $295.00

  • Delta Air Lines DL4688 / DL2548: MDW 2027-06-23 13:31:00 → MIA 2027-06-23 21:16:00; 1 stop(s) via DTW; 405 minutes. Local airport times.
    • DL4688: MDW 2027-06-23 13:31:00 → DTW 2027-06-23 15:44:00; layover at DTW: 150 minutes.
    • DL2548: DTW 2027-06-23 18:14:00 → MIA 2027-06-23 21:16:00.
  • Delta Air Lines DL2638 / DL4688: MIA 2027-06-26 08:05:00 → MDW 2027-06-26 13:01:00; 1 stop(s) via DTW; 356 minutes. Local airport times.
    • DL2638: MIA 2027-06-26 08:05:00 → DTW 2027-06-26 11:10:00; layover at DTW: 94 minutes.
    • DL4688: DTW 2027-06-26 12:44:00 → MDW 2027-06-26 13:01:00.

2027-06-23 → 2027-06-26 · $260.00

  • Southwest Airlines WN2383: MDW 2027-06-23 07:40:00 → MIA 2027-06-23 11:40:00; nonstop; 180 minutes. Local airport times.
  • Southwest Airlines WN2466: MIA 2027-06-26 15:00:00 → MDW 2027-06-26 17:10:00; nonstop; 190 minutes. Local airport times.

2027-06-23 → 2027-06-26 · $252.50

  • Southwest Airlines WN3002 / WN301: MDW 2027-06-23 07:40:00 → MIA 2027-06-23 15:05:00; 1 stop(s) via PIT; 385 minutes. Local airport times.
    • WN3002: MDW 2027-06-23 07:40:00 → PIT 2027-06-23 10:00:00; layover at PIT: 145 minutes.
    • WN301: PIT 2027-06-23 12:25:00 → MIA 2027-06-23 15:05:00.
  • Southwest Airlines WN2466: MIA 2027-06-26 15:00:00 → MDW 2027-06-26 17:10:00; nonstop; 190 minutes. Local airport times.

2027-06-23 → 2027-06-26 · $252.50

  • Southwest Airlines WN2897 / WN4284: MDW 2027-06-23 17:25:00 → MIA 2027-06-23 23:50:00; 1 stop(s) via BNA; 325 minutes. Local airport times.
    • WN2897: MDW 2027-06-23 17:25:00 → BNA 2027-06-23 18:50:00; layover at BNA: 100 minutes.
    • WN4284: BNA 2027-06-23 20:30:00 → MIA 2027-06-23 23:50:00.
  • Southwest Airlines WN2466: MIA 2027-06-26 15:00:00 → MDW 2027-06-26 17:10:00; nonstop; 190 minutes. Local airport times.

2027-06-23 → 2027-06-26 · $252.50

  • Southwest Airlines WN2959 / WN833: MDW 2027-06-23 07:35:00 → MIA 2027-06-23 14:35:00; 1 stop(s) via MCI; 360 minutes. Local airport times.
    • WN2959: MDW 2027-06-23 07:35:00 → MCI 2027-06-23 09:05:00; layover at MCI: 90 minutes.
    • WN833: MCI 2027-06-23 10:35:00 → MIA 2027-06-23 14:35:00.
  • Southwest Airlines WN2466: MIA 2027-06-26 15:00:00 → MDW 2027-06-26 17:10:00; nonstop; 190 minutes. Local airport times.

2027-06-23 → 2027-06-26 · $252.50

  • Southwest Airlines WN1908 / WN2643: MDW 2027-06-23 16:25:00 → MIA 2027-06-23 22:15:00; 1 stop(s) via MCO; 290 minutes. Local airport times.
    • WN1908: MDW 2027-06-23 16:25:00 → MCO 2027-06-23 20:00:00; layover at MCO: 60 minutes.
    • WN2643: MCO 2027-06-23 21:00:00 → MIA 2027-06-23 22:15:00.
  • Southwest Airlines WN2466: MIA 2027-06-26 15:00:00 → MDW 2027-06-26 17:10:00; nonstop; 190 minutes. Local airport times.

2027-06-23 → 2027-06-26 · $252.50

  • Southwest Airlines WN2737 / WN4943: MDW 2027-06-23 11:30:00 → MIA 2027-06-23 19:00:00; 1 stop(s) via STL; 390 minutes. Local airport times.
    • WN2737: MDW 2027-06-23 11:30:00 → STL 2027-06-23 12:40:00; layover at STL: 165 minutes.
    • WN4943: STL 2027-06-23 15:25:00 → MIA 2027-06-23 19:00:00.
  • Southwest Airlines WN2466: MIA 2027-06-26 15:00:00 → MDW 2027-06-26 17:10:00; nonstop; 190 minutes. Local airport times.

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For AI assistants

  • This page: Chicago (MDW) to Miami (MIA) · Jun 23, 2027 · return Jun 26, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
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  • 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 Chicago to Miami (MIA) 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. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. 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.