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Route overview: Chicago to San Diego (SAN) flight deals

Chicago (MDW) to San Diego (SAN), Nov 14–24, 2026: from $396 round trip

Chicago (MDW) to San Diego (SAN), Nov 14–24, 2026: from $396 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $396 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 14–24, 2026, 1 adult, economy, checked Oct 29, 2026.

MDW → SAN1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Sat, Nov 14 – Tue, Nov 24

Southwest Airlines
10:20 amMDW
4h 25m
Nonstop
12:45 pmSAN
Southwest Airlines
12:00 pmSAN
3h 55m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 14 – Tue, Nov 24

Southwest Airlines
3:15 pmMDW
4h 20m
Nonstop
5:35 pmSAN
Southwest Airlines
12:00 pmSAN
3h 55m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Sat, Nov 14 – Tue, Nov 24

Southwest Airlines
5:05 amMDW
6h 35m
PHX · 1h 25m
9:40 amSAN
Southwest Airlines
12:00 pmSAN
3h 55m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 14 – Tue, Nov 24

Southwest Airlines
1:20 pmMDW
7h 15m
CMH · 1h 20m
6:35 pmSAN
Southwest Airlines
12:00 pmSAN
3h 55m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 14 – Tue, Nov 24

Southwest Airlines
2:35 pmMDW
6h 10m
DEN · 1h 10m
6:45 pmSAN
Southwest Airlines
12:00 pmSAN
3h 55m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 14 – Tue, Nov 24

Southwest Airlines
3:45 pmMDW
7h 5m
ABQ · 1h 55m
8:50 pmSAN
Southwest Airlines
12:00 pmSAN
3h 55m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 14 – Tue, Nov 24

Southwest Airlines
9:55 amMDW
7h
BNA · 1h
2:55 pmSAN
Southwest Airlines
12:00 pmSAN
3h 55m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Sat, Nov 14 – Tue, Nov 24

Southwest Airlines
10:15 amMDW
7h 35m
HOU · 1h 35m
3:50 pmSAN
Southwest Airlines
12:00 pmSAN
3h 55m
Nonstop
5:55 pmMDW

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Hotels for these nights (Nov 14–24, 2026 · 10 nights · 2 adults, 1 room): 3★ Best Western Plus Oceanside Palms · 4★ The Seabird Ocean Resort & Spa, Part of Destination Hotel by Hyatt

Make this trip yours

MDW ⇄ SAN

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 13, 2026 · Return optionsNov 15, 2026 · Return optionsHotels in Oceanside, California with Axel
For AI assistants: every fare, every link, instructions

Chicago (MDW) to San Diego (SAN), Nov 14–24, 2026: from $396 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $396 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Nov 14–24, 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)
2026-11-14 → 2026-11-24Southwest AirlinesWN1456 / WN198110:20:00→12:45:00 4h 25m nonstop · 12:00:00→17:55:00 3h 55m nonstopAxel-exclusive $411.252026-10-29T01:29:13Z
2026-11-14 → 2026-11-24Southwest AirlinesWN4415 / WN198115:15:00→17:35:00 4h 20m nonstop · 12:00:00→17:55:00 3h 55m nonstopAxel-exclusive $411.252026-10-29T01:29:13Z
2026-11-14 → 2026-11-24Southwest AirlinesWN2995 + WN2447 / WN198105:05:00→09:40:00 6h 35m 1 stop via PHX · 12:00:00→17:55:00 3h 55m nonstopAxel-exclusive $396.252026-10-29T01:29:13Z
2026-11-14 → 2026-11-24Southwest AirlinesWN1354 + WN225 / WN198113:20:00→18:35:00 7h 15m 1 stop via CMH · 12:00:00→17:55:00 3h 55m nonstopAxel-exclusive $396.252026-10-29T01:29:13Z
2026-11-14 → 2026-11-24Southwest AirlinesWN4606 + WN1780 / WN198114:35:00→18:45:00 6h 10m 1 stop via DEN · 12:00:00→17:55:00 3h 55m nonstopAxel-exclusive $396.252026-10-29T01:29:13Z
2026-11-14 → 2026-11-24Southwest AirlinesWN153 + WN167 / WN198115:45:00→20:50:00 7h 05m 1 stop via ABQ · 12:00:00→17:55:00 3h 55m nonstopAxel-exclusive $396.252026-10-29T01:29:13Z
2026-11-14 → 2026-11-24Southwest AirlinesWN725 + WN1079 / WN198109:55:00→14:55:00 7h 00m 1 stop via BNA · 12:00:00→17:55:00 3h 55m nonstopAxel-exclusive $396.252026-10-29T01:29:13Z
2026-11-14 → 2026-11-24Southwest AirlinesWN4395 + WN3167 / WN198110:15:00→15:50:00 7h 35m 1 stop via HOU · 12:00:00→17:55:00 3h 55m nonstopAxel-exclusive $396.252026-10-29T01:29:13Z

Hotels in Oceanside, California for these trips

Hotels: under a trip, hotels in Oceanside, California 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 Oceanside, California

Route overview: Chicago to San Diego (SAN) flight deals

2026-11-14 → 2026-11-24 · Axel-exclusive $411.25

  • Southwest Airlines WN1456: MDW 2026-11-14 10:20:00 → SAN 2026-11-14 12:45:00; nonstop; 265 minutes. Local airport times.
  • Southwest Airlines WN1981: SAN 2026-11-24 12:00:00 → MDW 2026-11-24 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-14 → 2026-11-24 · Axel-exclusive $411.25

  • Southwest Airlines WN4415: MDW 2026-11-14 15:15:00 → SAN 2026-11-14 17:35:00; nonstop; 260 minutes. Local airport times.
  • Southwest Airlines WN1981: SAN 2026-11-24 12:00:00 → MDW 2026-11-24 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-14 → 2026-11-24 · Axel-exclusive $396.25

  • Southwest Airlines WN2995 / WN2447: MDW 2026-11-14 05:05:00 → SAN 2026-11-14 09:40:00; 1 stop(s) via PHX; 395 minutes. Local airport times.
    • WN2995: MDW 2026-11-14 05:05:00 → PHX 2026-11-14 07:55:00; layover at PHX: 85 minutes.
    • WN2447: PHX 2026-11-14 09:20:00 → SAN 2026-11-14 09:40:00.
  • Southwest Airlines WN1981: SAN 2026-11-24 12:00:00 → MDW 2026-11-24 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-14 → 2026-11-24 · Axel-exclusive $396.25

  • Southwest Airlines WN1354 / WN225: MDW 2026-11-14 13:20:00 → SAN 2026-11-14 18:35:00; 1 stop(s) via CMH; 435 minutes. Local airport times.
    • WN1354: MDW 2026-11-14 13:20:00 → CMH 2026-11-14 15:25:00; layover at CMH: 80 minutes.
    • WN225: CMH 2026-11-14 16:45:00 → SAN 2026-11-14 18:35:00.
  • Southwest Airlines WN1981: SAN 2026-11-24 12:00:00 → MDW 2026-11-24 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-14 → 2026-11-24 · Axel-exclusive $396.25

  • Southwest Airlines WN4606 / WN1780: MDW 2026-11-14 14:35:00 → SAN 2026-11-14 18:45:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
    • WN4606: MDW 2026-11-14 14:35:00 → DEN 2026-11-14 16:15:00; layover at DEN: 70 minutes.
    • WN1780: DEN 2026-11-14 17:25:00 → SAN 2026-11-14 18:45:00.
  • Southwest Airlines WN1981: SAN 2026-11-24 12:00:00 → MDW 2026-11-24 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-14 → 2026-11-24 · Axel-exclusive $396.25

  • Southwest Airlines WN153 / WN167: MDW 2026-11-14 15:45:00 → SAN 2026-11-14 20:50:00; 1 stop(s) via ABQ; 425 minutes. Local airport times.
    • WN153: MDW 2026-11-14 15:45:00 → ABQ 2026-11-14 17:55:00; layover at ABQ: 115 minutes.
    • WN167: ABQ 2026-11-14 19:50:00 → SAN 2026-11-14 20:50:00.
  • Southwest Airlines WN1981: SAN 2026-11-24 12:00:00 → MDW 2026-11-24 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-14 → 2026-11-24 · Axel-exclusive $396.25

  • Southwest Airlines WN725 / WN1079: MDW 2026-11-14 09:55:00 → SAN 2026-11-14 14:55:00; 1 stop(s) via BNA; 420 minutes. Local airport times.
    • WN725: MDW 2026-11-14 09:55:00 → BNA 2026-11-14 11:30:00; layover at BNA: 60 minutes.
    • WN1079: BNA 2026-11-14 12:30:00 → SAN 2026-11-14 14:55:00.
  • Southwest Airlines WN1981: SAN 2026-11-24 12:00:00 → MDW 2026-11-24 17:55:00; nonstop; 235 minutes. Local airport times.

2026-11-14 → 2026-11-24 · Axel-exclusive $396.25

  • Southwest Airlines WN4395 / WN3167: MDW 2026-11-14 10:15:00 → SAN 2026-11-14 15:50:00; 1 stop(s) via HOU; 455 minutes. Local airport times.
    • WN4395: MDW 2026-11-14 10:15:00 → HOU 2026-11-14 12:50:00; layover at HOU: 95 minutes.
    • WN3167: HOU 2026-11-14 14:25:00 → SAN 2026-11-14 15:50:00.
  • Southwest Airlines WN1981: SAN 2026-11-24 12:00:00 → MDW 2026-11-24 17:55:00; nonstop; 235 minutes. Local airport times.

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.

Explore this route

For AI assistants

  • This page: Chicago (MDW) to San Diego (SAN) · Nov 14, 2026 · return Nov 24, 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 Oceanside, California 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 Chicago to San Diego (SAN) 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.