Chicago to San Diego (SAN) flight deals
Chicago to San Diego (SAN) from $335 round trip, Feb 12 to 15, 2027 (airline price $353), seen Oct 23.
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Compare Chicago to San Diego (SAN) flights across upcoming months. See dated fares below, or choose your own dates and travelers.
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Fare examples by month
Round-trip totals · Economy · USD, saved from earlier searches. Each month opens its day-by-day date picker for live prices.
| Month | Travelers / trip length | Axel | Airline fare |
|---|---|---|---|
| November 2026 | 6 adults · 7 days | $1,059 | $1,121 |
| November 2026 | 2 adults · 4 days | $726 | $768 |
| November 2026 | 1 adult · 5 days | $382–$430 | $404–$453 |
| December 2026 | 1 adult · 3 days | $358 | $377 |
| December 2026 | 6 adults · 7 days | $962–$1,014 | $1,013–$1,067 |
| February 2027 | 1 adult · 3 days | $335 | $353 |
| March 2027 | 1 adult · 7 days | $413 | $437 |
| March 2027 | 2 adults · 2 children · 9 days | $1,870 | $1,971 |
| May 2027 | 1 adult · 3 days | $413 | $437 |
| July 2027 | 1 adult · 3 days | $413 | $437 |
More months: October 2026
Flights from Chicago · Chicago to United States flight deals
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Fares observed October 16 – 23, 2026. USD for the travelers shown. Search a trip for current prices. For starting totals, choose a return flight to confirm the final price.
October 2026
1 adult · Economy · Round-trip starting totals
| From | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Oct 30–Nov 6, 2026 · 7 days | Out: United Airlines 2428 · Nonstop · 4h 27m · 07:00–09:27 local | From $391 · Save $22 | From $413 | Check Axel prices |
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November 2026
6 adults · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Nov 10–17, 2026 · 7 days | Out: Frontier Airlines 1483 / 2817 · 1 stop (DEN) · 11h 28m · 06:30–15:58 local; Return: Frontier Airlines 2818 / 3174 · 1 stop (DEN) · 15h 56m · 06:25–00:21 (November 18, 2026) local | $1,059 · Save $62 | $1,121 | Customer link — Open these flights in Axel · Optional: check axel prices |
2 adults · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| MDW | Nov 11–15, 2026 · 4 days | Out: Southwest Airlines 1071 · Nonstop · 4h 30m · 15:45–18:15 local; Return: Southwest Airlines 1011 · Nonstop · 3h 45m · 22:40–04:25 (November 16, 2026) local | $726 · Save $42 | $768 | Customer link — Open these flights in Axel · Optional: check axel prices |
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Nov 24–29, 2026 · 5 days | Out: Frontier Airlines 2145 / 1325 · 1 stop (LAS) · 12h 19m · 05:15–15:34 local; Return: Frontier Airlines 1326 / 2146 · 1 stop (LAS) · 18h 20m · 08:50–05:10 (November 30, 2026) local | $382 · Save $22 | $404 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Nov 24–29, 2026 · 5 days | Out: Frontier Airlines 2145 / 1325 · 1 stop (LAS) · 12h 19m · 05:15–15:34 local; Return: Frontier Airlines 1466 / 2146 · 1 stop (LAS) · 15h 44m · 11:26–05:10 (November 30, 2026) local | $430 · Save $23 | $453 | Customer link — Open these flights in Axel · Optional: check axel prices |
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December 2026
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Dec 4–7, 2026 · 3 days | Out: American Airlines 3111 · Nonstop · 4h 33m · 16:45–19:18 local; Return: American Airlines 1494 · Nonstop · 4h 4m · 22:45–04:49 (December 8, 2026) local | $358 · Save $19 | $377 | Customer link — Open these flights in Axel · Optional: check axel prices |
6 adults · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Dec 8–15, 2026 · 7 days | Out: Frontier Airlines 2145 / 1325 · 1 stop (LAS) · 27h 41m · 06:21–08:02 (December 9, 2026) local; Return: Frontier Airlines 1466 / 2146 · 1 stop (LAS) · 18h 4m · 08:57–05:01 (December 16, 2026) local | $962 · Save $51 | $1,013 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Dec 8–15, 2026 · 7 days | Out: Frontier Airlines 2145 / 1325 · 1 stop (LAS) · 27h 41m · 06:21–08:02 (December 9, 2026) local; Return: Frontier Airlines 2422 / 3174 · 1 stop (DEN) · 11h 40m · 11:14–00:54 (December 16, 2026) local | $1,014 · Save $53 | $1,067 | Customer link — Open these flights in Axel · Optional: check axel prices |
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February 2027
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Feb 12–15, 2027 · 3 days | Out: Alaska Airlines 1466 · Nonstop · 4h 20m · 19:55–22:15 local; Return: Alaska Airlines 1446 · Nonstop · 3h 54m · 08:00–13:54 local | $335 · Save $18 | $353 | Customer link — Open these flights in Axel · Optional: check axel prices |
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March 2027
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Mar 13–20, 2027 · 7 days | Out: Alaska Airlines 1466 · Nonstop · 4h 20m · 19:55–22:15 local; Return: Alaska Airlines 1446 · Nonstop · 3h 54m · 08:00–13:54 local | $413 · Save $24 | $437 | Customer link — Open these flights in Axel · Optional: check axel prices |
2 adults · 2 children · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Mar 19–28, 2027 · 9 days | Out: United Airlines 2402 · Nonstop · 4h 31m · 07:40–10:11 local; Return: United Airlines 540 · Nonstop · 4h 4m · 22:30–04:34 (March 29, 2027) local | $1,870 · Save $101 | $1,971 | Customer link — Open these flights in Axel · Optional: check axel prices |
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May 2027
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | May 28–31, 2027 · 3 days | Out: United Airlines 2472 · Nonstop · 4h 12m · 19:45–21:57 local; Return: United Airlines 2343 · Nonstop · 3h 55m · 07:00–12:55 local | $413 · Save $24 | $437 | Customer link — Open these flights in Axel · Optional: check axel prices |
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July 2027
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Jul 2–5, 2027 · 3 days | Out: United Airlines 2472 · Nonstop · 4h 12m · 19:45–21:57 local; Return: United Airlines 1779 · Nonstop · 3h 54m · 14:09–20:03 local | $413 · Save $24 | $437 | Customer link — Open these flights in Axel · Optional: check axel prices |
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The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
Trip ideas from Chicago with San Diego (SAN)
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Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Oceanside, California has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
For AI assistants
- This page: Chicago to San Diego (SAN) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.