Travel with Axel,
get the best price.

Route overview: Orlando to Chicago (MDW) flight deals

Orlando → Chicago

May 29, 2027 · return Jun 5, 2027

MCO → MDW1 adulteconomyRound trip

9 flight options · 3 airlines

Nonstop flights

Sat, May 29 – Sat, Jun 5

Frontier Airlines
5:29 pmMCO
3h 1m
Nonstop
7:30 pmMDW
Frontier Airlines
6:11 pmMDW
2h 49m
Nonstop
10:00 pmMCO

Round-trip total · 1 adult · Taxes included

Sat, May 29 – Sat, Jun 5

Southwest Airlines
4:35 pmMCO
2h 55m
Nonstop
6:30 pmMDW
Southwest Airlines
7:50 amMDW
2h 45m
Nonstop
11:35 amMCO

Round-trip total · 1 adult · Taxes included

Sat, May 29 – Sat, Jun 5

Southwest Airlines
10:10 amMCO
2h 55m
Nonstop
12:05 pmMDW
Southwest Airlines
7:50 amMDW
2h 45m
Nonstop
11:35 amMCO

Round-trip total · 1 adult · Taxes included

One-stop flights

Sat, May 29 – Sat, Jun 5

Delta Air Lines
5:45 pmMCO
5h 32m
ATL · 1h 55m
10:17 pmMDW
Delta Air Lines
1:31 pmMDW
5h 3m
DTW · 1h 6m
7:34 pmMCO

Round-trip total · 1 adult · Taxes included

Sat, May 29 – Sat, Jun 5

Frontier Airlines
7:10 amMCO
5h 23m
ATL · 1h 13m
11:33 amMDW
Frontier Airlines
6:11 pmMDW
2h 49m
Nonstop
10:00 pmMCO

Round-trip total · 1 adult · Taxes included

Sat, May 29 – Sat, Jun 5

Southwest Airlines
3:40 pmMCO
5h 10m
SDF · 1h 35m
7:50 pmMDW
Southwest Airlines
7:50 amMDW
2h 45m
Nonstop
11:35 amMCO

Round-trip total · 1 adult · Taxes included

Sat, May 29 – Sat, Jun 5

Southwest Airlines
4:00 pmMCO
5h 10m
PIT · 1h 15m
8:10 pmMDW
Southwest Airlines
7:50 amMDW
2h 45m
Nonstop
11:35 amMCO

Round-trip total · 1 adult · Taxes included

Sat, May 29 – Sat, Jun 5

Southwest Airlines
10:40 amMCO
5h 20m
RSW · 1h 20m
3:00 pmMDW
Southwest Airlines
7:50 amMDW
2h 45m
Nonstop
11:35 amMCO

Round-trip total · 1 adult · Taxes included

Sat, May 29 – Sat, Jun 5

Southwest Airlines
8:10 amMCO
4h 55m
STL · 1h 10m
12:05 pmMDW
Southwest Airlines
7:50 amMDW
2h 45m
Nonstop
11:35 amMCO

Round-trip total · 1 adult · Taxes included

Make this trip yours

MCO ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

No account needed to see prices.

Already have an account? Log in

Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Frontier Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • Not satisfied? Full refund.If you are unhappy with the experience for any reason, or simply change your mind, cancel within 24 hours of booking (departure 7+ days away) and we refund you in full. We stand by our product. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

Explore this route

All dates for this routeMay 28, 2027 → Jun 4, 2027May 30, 2027 → Jun 6, 2027
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: Orlando to Chicago (MDW) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-05-29 → 2027-06-05Frontier AirlinesF91457 / F91536$220.382026-10-29T01:28:44Z
2027-05-29 → 2027-06-05Southwest AirlinesWN2805 / WN4565$322.502026-10-29T01:28:44Z
2027-05-29 → 2027-06-05Delta Air LinesDL1150 + DL1076 / DL4688 + DL1274$408.502026-10-29T01:28:44Z
2027-05-29 → 2027-06-05Southwest AirlinesWN2803 / WN4565$322.502026-10-29T01:28:44Z
2027-05-29 → 2027-06-05Frontier AirlinesF91563 + F92779 / F91536$249.132026-10-29T01:28:44Z
2027-05-29 → 2027-06-05Southwest AirlinesWN1915 + WN282 / WN4565$334.002026-10-29T01:28:44Z
2027-05-29 → 2027-06-05Southwest AirlinesWN2840 + WN3556 / WN4565$334.002026-10-29T01:28:44Z
2027-05-29 → 2027-06-05Southwest AirlinesWN2777 + WN2106 / WN4565$334.002026-10-29T01:28:44Z
2027-05-29 → 2027-06-05Southwest AirlinesWN1789 + WN287 / WN4565$334.002026-10-29T01:28:44Z

2027-05-29 → 2027-06-05 · $220.38

  • Frontier Airlines F91457: MCO 2027-05-29 17:29:00 → MDW 2027-05-29 19:30:00; nonstop; 181 minutes. Local airport times.
  • Frontier Airlines F91536: MDW 2027-06-05 18:11:00 → MCO 2027-06-05 22:00:00; nonstop; 169 minutes. Local airport times.

2027-05-29 → 2027-06-05 · $322.50

  • Southwest Airlines WN2805: MCO 2027-05-29 16:35:00 → MDW 2027-05-29 18:30:00; nonstop; 175 minutes. Local airport times.
  • Southwest Airlines WN4565: MDW 2027-06-05 07:50:00 → MCO 2027-06-05 11:35:00; nonstop; 165 minutes. Local airport times.

2027-05-29 → 2027-06-05 · $408.50

  • Delta Air Lines DL1150 / DL1076: MCO 2027-05-29 17:45:00 → MDW 2027-05-29 22:17:00; 1 stop(s) via ATL; 332 minutes. Local airport times.
    • DL1150: MCO 2027-05-29 17:45:00 → ATL 2027-05-29 19:25:00; layover at ATL: 115 minutes.
    • DL1076: ATL 2027-05-29 21:20:00 → MDW 2027-05-29 22:17:00.
  • Delta Air Lines DL4688 / DL1274: MDW 2027-06-05 13:31:00 → MCO 2027-06-05 19:34:00; 1 stop(s) via DTW; 303 minutes. Local airport times.
    • DL4688: MDW 2027-06-05 13:31:00 → DTW 2027-06-05 15:44:00; layover at DTW: 66 minutes.
    • DL1274: DTW 2027-06-05 16:50:00 → MCO 2027-06-05 19:34:00.

2027-05-29 → 2027-06-05 · $322.50

  • Southwest Airlines WN2803: MCO 2027-05-29 10:10:00 → MDW 2027-05-29 12:05:00; nonstop; 175 minutes. Local airport times.
  • Southwest Airlines WN4565: MDW 2027-06-05 07:50:00 → MCO 2027-06-05 11:35:00; nonstop; 165 minutes. Local airport times.

2027-05-29 → 2027-06-05 · $249.13

  • Frontier Airlines F91563 / F92779: MCO 2027-05-29 07:10:00 → MDW 2027-05-29 11:33:00; 1 stop(s) via ATL; 323 minutes. Local airport times.
    • F91563: MCO 2027-05-29 07:10:00 → ATL 2027-05-29 09:14:00; layover at ATL: 73 minutes.
    • F92779: ATL 2027-05-29 10:27:00 → MDW 2027-05-29 11:33:00.
  • Frontier Airlines F91536: MDW 2027-06-05 18:11:00 → MCO 2027-06-05 22:00:00; nonstop; 169 minutes. Local airport times.

2027-05-29 → 2027-06-05 · $334.00

  • Southwest Airlines WN1915 / WN282: MCO 2027-05-29 15:40:00 → MDW 2027-05-29 19:50:00; 1 stop(s) via SDF; 310 minutes. Local airport times.
    • WN1915: MCO 2027-05-29 15:40:00 → SDF 2027-05-29 18:00:00; layover at SDF: 95 minutes.
    • WN282: SDF 2027-05-29 19:35:00 → MDW 2027-05-29 19:50:00.
  • Southwest Airlines WN4565: MDW 2027-06-05 07:50:00 → MCO 2027-06-05 11:35:00; nonstop; 165 minutes. Local airport times.

2027-05-29 → 2027-06-05 · $334.00

  • Southwest Airlines WN2840 / WN3556: MCO 2027-05-29 16:00:00 → MDW 2027-05-29 20:10:00; 1 stop(s) via PIT; 310 minutes. Local airport times.
    • WN2840: MCO 2027-05-29 16:00:00 → PIT 2027-05-29 18:25:00; layover at PIT: 75 minutes.
    • WN3556: PIT 2027-05-29 19:40:00 → MDW 2027-05-29 20:10:00.
  • Southwest Airlines WN4565: MDW 2027-06-05 07:50:00 → MCO 2027-06-05 11:35:00; nonstop; 165 minutes. Local airport times.

2027-05-29 → 2027-06-05 · $334.00

  • Southwest Airlines WN2777 / WN2106: MCO 2027-05-29 10:40:00 → MDW 2027-05-29 15:00:00; 1 stop(s) via RSW; 320 minutes. Local airport times.
    • WN2777: MCO 2027-05-29 10:40:00 → RSW 2027-05-29 11:45:00; layover at RSW: 80 minutes.
    • WN2106: RSW 2027-05-29 13:05:00 → MDW 2027-05-29 15:00:00.
  • Southwest Airlines WN4565: MDW 2027-06-05 07:50:00 → MCO 2027-06-05 11:35:00; nonstop; 165 minutes. Local airport times.

2027-05-29 → 2027-06-05 · $334.00

  • Southwest Airlines WN1789 / WN287: MCO 2027-05-29 08:10:00 → MDW 2027-05-29 12:05:00; 1 stop(s) via STL; 295 minutes. Local airport times.
    • WN1789: MCO 2027-05-29 08:10:00 → STL 2027-05-29 09:45:00; layover at STL: 70 minutes.
    • WN287: STL 2027-05-29 10:55:00 → MDW 2027-05-29 12:05:00.
  • Southwest Airlines WN4565: MDW 2027-06-05 07:50:00 → MCO 2027-06-05 11:35:00; nonstop; 165 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Orlando (MCO) to Chicago (MDW) · May 29, 2027 · return Jun 5, 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.
  • 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 Orlando 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. 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.