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San Diego → Chicago

Jun 25, 2027 · return Jun 28, 2027

SAN → MDW1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Fri, Jun 25 – Mon, Jun 28

Southwest Airlines
10:40 pmSAN
3h 45m
Nonstop
4:25 am+1MDW
Southwest Airlines
8:55 pmMDW
4h 30m
Nonstop
11:25 pmSAN

Round-trip total · 1 adult · Taxes included

Fri, Jun 25 – Mon, Jun 28

Southwest Airlines
11:45 amSAN
3h 55m
Nonstop
5:40 pmMDW
Southwest Airlines
8:55 pmMDW
4h 30m
Nonstop
11:25 pmSAN

Round-trip total · 1 adult · Taxes included

One-stop flights

Fri, Jun 25 – Mon, Jun 28

Southwest Airlines
11:55 amSAN
6h 5m
STL · 1h 30m
8:00 pmMDW
Southwest Airlines
8:55 pmMDW
4h 30m
Nonstop
11:25 pmSAN

Round-trip total · 1 adult · Taxes included

Fri, Jun 25 – Mon, Jun 28

Southwest Airlines
12:30 pmSAN
7h
DEN · 2h 15m
9:30 pmMDW
Southwest Airlines
8:55 pmMDW
4h 30m
Nonstop
11:25 pmSAN

Round-trip total · 1 adult · Taxes included

Fri, Jun 25 – Mon, Jun 28

Southwest Airlines
12:10 pmSAN
5h 35m
OMA · 1h 5m
7:45 pmMDW
Southwest Airlines
8:55 pmMDW
4h 30m
Nonstop
11:25 pmSAN

Round-trip total · 1 adult · Taxes included

Fri, Jun 25 – Mon, Jun 28

Southwest Airlines
11:55 amSAN
7h 10m
BNA · 1h 45m
9:05 pmMDW
Southwest Airlines
8:55 pmMDW
4h 30m
Nonstop
11:25 pmSAN

Round-trip total · 1 adult · Taxes included

Fri, Jun 25 – Mon, Jun 28

Southwest Airlines
8:25 amSAN
6h 20m
SLC · 1h 10m
4:45 pmMDW
Southwest Airlines
8:55 pmMDW
4h 30m
Nonstop
11:25 pmSAN

Round-trip total · 1 adult · Taxes included

Fri, Jun 25 – Mon, Jun 28

Southwest Airlines
8:10 amSAN
7h 10m
AUS · 1h 50m
5:20 pmMDW
Southwest Airlines
8:55 pmMDW
4h 30m
Nonstop
11:25 pmSAN

Round-trip total · 1 adult · Taxes included

Make this trip yours

SAN ⇄ 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)
2027-06-25 → 2027-06-28Southwest AirlinesWN1011 / WN1987$425.002026-10-29T02:06:00Z
2027-06-25 → 2027-06-28Southwest AirlinesWN1156 / WN1987$425.002026-10-29T02:06:00Z
2027-06-25 → 2027-06-28Southwest AirlinesWN4711 + WN4175 / WN1987$410.002026-10-29T02:06:00Z
2027-06-25 → 2027-06-28Southwest AirlinesWN3699 + WN776 / WN1987$410.002026-10-29T02:06:00Z
2027-06-25 → 2027-06-28Southwest AirlinesWN399 + WN1407 / WN1987$410.002026-10-29T02:06:00Z
2027-06-25 → 2027-06-28Southwest AirlinesWN4669 + WN651 / WN1987$410.002026-10-29T02:06:00Z
2027-06-25 → 2027-06-28Southwest AirlinesWN3752 + WN4349 / WN1987$410.002026-10-29T02:06:00Z
2027-06-25 → 2027-06-28Southwest AirlinesWN3681 + WN295 / WN1987$410.002026-10-29T02:06:00Z

2027-06-25 → 2027-06-28 · $425.00

  • Southwest Airlines WN1011: SAN 2027-06-25 22:40:00 → MDW 2027-06-26 04:25:00; nonstop; 225 minutes. Local airport times.
  • Southwest Airlines WN1987: MDW 2027-06-28 20:55:00 → SAN 2027-06-28 23:25:00; nonstop; 270 minutes. Local airport times.

2027-06-25 → 2027-06-28 · $425.00

  • Southwest Airlines WN1156: SAN 2027-06-25 11:45:00 → MDW 2027-06-25 17:40:00; nonstop; 235 minutes. Local airport times.
  • Southwest Airlines WN1987: MDW 2027-06-28 20:55:00 → SAN 2027-06-28 23:25:00; nonstop; 270 minutes. Local airport times.

2027-06-25 → 2027-06-28 · $410.00

  • Southwest Airlines WN4711 / WN4175: SAN 2027-06-25 11:55:00 → MDW 2027-06-25 20:00:00; 1 stop(s) via STL; 365 minutes. Local airport times.
    • WN4711: SAN 2027-06-25 11:55:00 → STL 2027-06-25 17:25:00; layover at STL: 90 minutes.
    • WN4175: STL 2027-06-25 18:55:00 → MDW 2027-06-25 20:00:00.
  • Southwest Airlines WN1987: MDW 2027-06-28 20:55:00 → SAN 2027-06-28 23:25:00; nonstop; 270 minutes. Local airport times.

2027-06-25 → 2027-06-28 · $410.00

  • Southwest Airlines WN3699 / WN776: SAN 2027-06-25 12:30:00 → MDW 2027-06-25 21:30:00; 1 stop(s) via DEN; 420 minutes. Local airport times.
    • WN3699: SAN 2027-06-25 12:30:00 → DEN 2027-06-25 15:50:00; layover at DEN: 135 minutes.
    • WN776: DEN 2027-06-25 18:05:00 → MDW 2027-06-25 21:30:00.
  • Southwest Airlines WN1987: MDW 2027-06-28 20:55:00 → SAN 2027-06-28 23:25:00; nonstop; 270 minutes. Local airport times.

2027-06-25 → 2027-06-28 · $410.00

  • Southwest Airlines WN399 / WN1407: SAN 2027-06-25 12:10:00 → MDW 2027-06-25 19:45:00; 1 stop(s) via OMA; 335 minutes. Local airport times.
    • WN399: SAN 2027-06-25 12:10:00 → OMA 2027-06-25 17:15:00; layover at OMA: 65 minutes.
    • WN1407: OMA 2027-06-25 18:20:00 → MDW 2027-06-25 19:45:00.
  • Southwest Airlines WN1987: MDW 2027-06-28 20:55:00 → SAN 2027-06-28 23:25:00; nonstop; 270 minutes. Local airport times.

2027-06-25 → 2027-06-28 · $410.00

  • Southwest Airlines WN4669 / WN651: SAN 2027-06-25 11:55:00 → MDW 2027-06-25 21:05:00; 1 stop(s) via BNA; 430 minutes. Local airport times.
    • WN4669: SAN 2027-06-25 11:55:00 → BNA 2027-06-25 17:45:00; layover at BNA: 105 minutes.
    • WN651: BNA 2027-06-25 19:30:00 → MDW 2027-06-25 21:05:00.
  • Southwest Airlines WN1987: MDW 2027-06-28 20:55:00 → SAN 2027-06-28 23:25:00; nonstop; 270 minutes. Local airport times.

2027-06-25 → 2027-06-28 · $410.00

  • Southwest Airlines WN3752 / WN4349: SAN 2027-06-25 08:25:00 → MDW 2027-06-25 16:45:00; 1 stop(s) via SLC; 380 minutes. Local airport times.
    • WN3752: SAN 2027-06-25 08:25:00 → SLC 2027-06-25 11:35:00; layover at SLC: 70 minutes.
    • WN4349: SLC 2027-06-25 12:45:00 → MDW 2027-06-25 16:45:00.
  • Southwest Airlines WN1987: MDW 2027-06-28 20:55:00 → SAN 2027-06-28 23:25:00; nonstop; 270 minutes. Local airport times.

2027-06-25 → 2027-06-28 · $410.00

  • Southwest Airlines WN3681 / WN295: SAN 2027-06-25 08:10:00 → MDW 2027-06-25 17:20:00; 1 stop(s) via AUS; 430 minutes. Local airport times.
    • WN3681: SAN 2027-06-25 08:10:00 → AUS 2027-06-25 13:00:00; layover at AUS: 110 minutes.
    • WN295: AUS 2027-06-25 14:50:00 → MDW 2027-06-25 17:20:00.
  • Southwest Airlines WN1987: MDW 2027-06-28 20:55:00 → SAN 2027-06-28 23:25:00; nonstop; 270 minutes. Local airport times.

More dates for this route