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Milwaukee → Chicago

Aug 21, 2027 · return Aug 28, 2027

MKE → MDW1 adulteconomyRound trip

2 flight options · 1 airline

Nonstop flights

Sat, Aug 21 – Sat, Aug 28

Southwest Airlines
4:45 pmMKE
50m
Nonstop
5:35 pmMDW
Southwest Airlines
10:10 amMDW
50m
Nonstop
11:00 amMKE

Round-trip total · 1 adult · Taxes included

Sat, Aug 21 – Sat, Aug 28

Southwest Airlines
5:40 amMKE
1h 5m
Nonstop
6:45 amMDW
Southwest Airlines
10:10 amMDW
50m
Nonstop
11:00 amMKE

Round-trip total · 1 adult · Taxes included

Make this trip yours

MKE ⇄ MDW

Economy

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

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More dates

All dates for this routeNov 5, 2026 → Nov 8, 2026Nov 14, 2026 → Nov 21, 2026Nov 24, 2026 → Nov 29, 2026Dec 5, 2026 → Dec 12, 2026Dec 17, 2026 → Dec 20, 2026Dec 26, 2026 → Jan 2, 2027Jan 5, 2027 · One wayJan 16, 2027 → Jan 23, 2027Feb 5, 2027 → Feb 8, 2027Apr 3, 2027 → Apr 10, 2027Jun 26, 2027 → Jul 3, 2027Sep 17, 2027 → Sep 20, 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.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-08-21 → 2027-08-28Southwest AirlinesWN496 / WN598$249.002026-10-29T01:30:18Z
2027-08-21 → 2027-08-28Southwest AirlinesWN4802 / WN598$249.002026-10-29T01:30:18Z

2027-08-21 → 2027-08-28 · $249.00

  • Southwest Airlines WN496: MKE 2027-08-21 16:45:00 → MDW 2027-08-21 17:35:00; nonstop; 50 minutes. Local airport times.
  • Southwest Airlines WN598: MDW 2027-08-28 10:10:00 → MKE 2027-08-28 11:00:00; nonstop; 50 minutes. Local airport times.

2027-08-21 → 2027-08-28 · $249.00

  • Southwest Airlines WN4802: MKE 2027-08-21 05:40:00 → MDW 2027-08-21 06:45:00; nonstop; 65 minutes. Local airport times.
  • Southwest Airlines WN598: MDW 2027-08-28 10:10:00 → MKE 2027-08-28 11:00:00; nonstop; 50 minutes. Local airport times.

More dates for this route