Prices may change. Select and confirm the full itinerary with the booking provider. Dates can differ between airport cards.
A great San Diego trip starts with a fare worth finding. Compare the latest samples below, then join our upcoming free newsletter to get standout Chicago flight finds in your inbox.
Same airports & dates. Each provider checks its own current prices.
ORD → SAN · Dec 2–Dec 9
Search fare; select your return flight to confirm.
Spend more on being in San Diego, and less on getting there. These are real examples from our research—the reason it pays to keep an eye on the fares.
$249 for Dec 2–Dec 9, 2026, compared with $417 for Jul 23–Jul 30, 2027.
12 seven-night date pairs from ORD to the same arrival-airport set (SAN). Lowest returned fare per date pair; checks within 24 hours. Airlines, stops and ticket conditions can differ. A travel-date comparison, not a booking-time prediction.
Explore the cheaper date samples ↗The same dated search ranged from $194 to $297 across 61 historical price observations.
ORD → SAN · Dec 2–Dec 9, 2026. Google Flights history covers Jul 29, 2026–Sep 27, 2026. The percentage is the low below the high. This does not prove when you should book or what subscribers will save.
See the price history ↗ORD → SAN · Dec 2–Dec 9, 2026. Recorded Sep 27, 2026.
Our archive starts Sep 27, 2026 and contains 263 seven-night fare observations for this route. Search fare; return may require confirmation. This is our record, not an industry-wide all-time low or a current offer.
How we keep fare records ↗Our upcoming free newsletter will bring standout Chicago flight finds to your inbox. Less checking. More trip planning.
Same dates: Dec 2–Dec 9. Same arrival airports: SAN.
1 stop outbound
Nonstop outbound
$48 separates the lowest and highest airport sample for these dates. These are search-result fares for seven-night trips. Flight times, stops and baggage can differ. Ground transport is excluded.
Across 12 matched date pairs in this sample, ORD had the lowest airport fare 12 time(s); MDW had the lowest airport fare 2 time(s). Ties count for each airport. This describes the sampled dates only.
A cheaper ticket can come with a pricier ride. Add your own round-trip transport estimate to the matched fares.
Flight sample $353
$353fare + transportFlight sample $406
$406fare + transportAdd your transport estimates to compare your total.
One adult, economy, USD. The two fares use identical dates and arrival-airport sets, checked within 24 hours. Transport starts at $0 because we don’t know your starting point. Baggage and other extras are excluded. Prices and itineraries can differ.
ORD → SAN, Mar 15. Nonstop.
Across 24 seven-night airport/date searches. Includes connecting carriers.
Lowest: $249, Dec 2–Dec 9 from ORD.
MDW, ORD in these outbound results. This is not a full schedule.
Derived from the current seven-night observations on this page. Outbound times describe the outbound journey only; fare amounts are round-trip search results. See sources and coverage.
Lowest fare in each sampled departure month. Seven-night trips only.
Swipe to see more months →
Tap a bar to see the dates, airports and check time behind that sample.
| Departure month | Lowest sample | Date pairs |
|---|---|---|
| 2026-10 | $353 | 1 |
| 2026-11 | $308 | 1 |
| 2026-12 | $249 | 2 |
| 2027-01 | $259 | 1 |
| 2027-02 | $274 | 1 |
| 2027-03 | $417 | 1 |
| 2027-04 | $395 | 1 |
| 2027-05 | $417 | 1 |
| 2027-06 | $395 | 2 |
| 2027-07 | $417 | 1 |
Sampled dates, not a complete fare calendar. Each month can have different date coverage. This chart describes future travel dates, not past price movements.
Prices checked within seven days. Use the filters to find a trip that fits.
| Dates / airports | Airline / outbound | Round trip | Check price |
|---|---|---|---|
| Dec 2–Dec 9ORD → SAN · 7 nights |  Frontier1 stop · 18h 57m | $249Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jan 23–Jan 30ORD → SAN · 7 nights | Frontier1 stop · 12h 10m | $259Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Feb 18–Feb 25ORD → SAN · 7 nights | Frontier1 stop · 9h 8m | $274Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 2–Dec 9ORD → SAN · 7 nights |  AmericanNonstop · 4h 39m | $297Return also checkedChecked Sep 27 | Google Skyscanner ↗ItineraryORD → SAN SAN → ORD |
| Dec 2–Dec 9MDW → SAN · 7 nights |  SouthwestNonstop · 4h 30m | $297Return also checkedChecked Sep 27 | Google Skyscanner ↗ItineraryMDW → SAN SAN → MDW |
| Jan 23–Jan 30MDW → SAN · 7 nights | SouthwestNonstop · 4h 30m | $297Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 2–Dec 9ORD → SAN · 7 nights |  AlaskaNonstop · 4h 45m | $297Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jan 23–Jan 30ORD → SAN · 7 nights |  UnitedNonstop · 4h 36m | $297Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jan 23–Jan 30ORD → SAN · 7 nights | AmericanNonstop · 4h 39m | $297Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jan 23–Jan 30ORD → SAN · 7 nights | AlaskaNonstop · 4h 38m | $297Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Oct 25–Oct 28MDW → SAN · 3 nights | SouthwestNonstop · 4h 25m | $307Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Oct 25–Oct 28ORD → SAN · 3 nights | UnitedNonstop · 4h 27m | $307Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Oct 25–Oct 28ORD → SAN · 3 nights | AlaskaNonstop · 4h 36m | $307Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Oct 25–Oct 28ORD → SAN · 3 nights | AmericanNonstop · 4h 33m | $307Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 2–Dec 9MDW → SAN · 7 nights | Southwest1 stop · 6h 5m | $307Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jan 23–Jan 30MDW → SAN · 7 nights | Southwest1 stop · 6h 10m | $307Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jan 23–Jan 30ORD → SAN · 7 nights | United1 stop · 6h 8m | $307Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Nov 6–Nov 13ORD → SAN · 7 nights | Frontier1 stop · 19h 27m | $308Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Nov 6–Nov 13MDW → SAN · 7 nights | SouthwestNonstop · 4h 25m | $337Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Feb 18–Feb 25MDW → SAN · 7 nights | SouthwestNonstop · 4h 30m | $337Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Oct 11–Oct 18ORD → SAN · 7 nights | Frontier1 stop · 19h 26m | $353Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 28–Jan 4ORD → SAN · 7 nights | AmericanNonstop · 4h 35m | $388Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Apr 10–Apr 17MDW → SAN · 7 nights | SouthwestNonstop · 4h 30m | $395Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Apr 10–Apr 17ORD → SAN · 7 nights | AlaskaNonstop · 4h 25m | $395Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jun 1–Jun 8ORD → SAN · 7 nights | AlaskaNonstop · 4h 25m | $395Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Oct 11–Oct 18MDW → SAN · 7 nights | SouthwestNonstop · 4h 25m | $406Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Mar 15–Mar 22ORD → SAN · 7 nights | AmericanNonstop · 4h 30m | $417Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| May 6–May 13MDW → SAN · 7 nights | SouthwestNonstop · 4h 25m | $417Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| May 6–May 13ORD → SAN · 7 nights | AlaskaNonstop · 4h 25m | $417Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jun 27–Jul 4ORD → SAN · 7 nights | AlaskaNonstop · 4h 25m | $417Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jul 23–Jul 30ORD → SAN · 7 nights | AlaskaNonstop · 4h 25m | $417Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Dec 28–Jan 4MDW → SAN · 7 nights | SouthwestNonstop · 4h 30m | $436Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jun 1–Jun 8MDW → SAN · 7 nights | SouthwestNonstop · 4h 25m | $438Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Mar 15–Mar 22MDW → SAN · 7 nights | SouthwestNonstop · 4h 30m | $447Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jul 23–Jul 30MDW → SAN · 7 nights |  Delta1 stop · 7h 27m | $458Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
| Jun 27–Jul 4MDW → SAN · 7 nights | Delta1 stop · 10h 36m | $688Select return to confirmChecked Sep 27 | Google Skyscanner ↗ |
No samples match these filters. Try another airport or trip length.
Prices can change. Cabin baggage and checked bags are not assumed included. Confirm the complete itinerary, airline fare rules and final price on the booking site.
ORD → SAN · Dec 2–Dec 9, 2026
| Observation date | Price |
|---|---|
| Jul 29, 2026 | $237 |
| Jul 30, 2026 | $237 |
| Jul 31, 2026 | $237 |
| Aug 1, 2026 | $279 |
| Aug 2, 2026 | $279 |
| Aug 3, 2026 | $279 |
| Aug 4, 2026 | $279 |
| Aug 5, 2026 | $279 |
| Aug 6, 2026 | $279 |
| Aug 7, 2026 | $279 |
| Aug 8, 2026 | $279 |
| Aug 9, 2026 | $297 |
| Aug 10, 2026 | $243 |
| Aug 11, 2026 | $243 |
| Aug 12, 2026 | $243 |
| Aug 13, 2026 | $243 |
| Aug 14, 2026 | $243 |
| Aug 15, 2026 | $277 |
| Aug 16, 2026 | $277 |
| Aug 17, 2026 | $277 |
| Aug 18, 2026 | $271 |
| Aug 19, 2026 | $266 |
| Aug 20, 2026 | $262 |
| Aug 21, 2026 | $262 |
| Aug 22, 2026 | $262 |
| Aug 23, 2026 | $262 |
| Aug 24, 2026 | $217 |
| Aug 25, 2026 | $217 |
| Aug 26, 2026 | $217 |
| Aug 27, 2026 | $217 |
| Aug 28, 2026 | $217 |
| Aug 29, 2026 | $276 |
| Aug 30, 2026 | $276 |
| Aug 31, 2026 | $276 |
| Sep 1, 2026 | $238 |
| Sep 2, 2026 | $238 |
| Sep 3, 2026 | $238 |
| Sep 4, 2026 | $238 |
| Sep 5, 2026 | $271 |
| Sep 6, 2026 | $276 |
| Sep 7, 2026 | $276 |
| Sep 8, 2026 | $276 |
| Sep 9, 2026 | $257 |
| Sep 10, 2026 | $257 |
| Sep 11, 2026 | $257 |
| Sep 12, 2026 | $276 |
| Sep 13, 2026 | $277 |
| Sep 14, 2026 | $233 |
| Sep 15, 2026 | $220 |
| Sep 16, 2026 | $194 |
| Sep 17, 2026 | $194 |
| Sep 18, 2026 | $194 |
| Sep 19, 2026 | $228 |
| Sep 20, 2026 | $228 |
| Sep 21, 2026 | $238 |
| Sep 22, 2026 | $238 |
| Sep 23, 2026 | $238 |
| Sep 24, 2026 | $238 |
| Sep 25, 2026 | $238 |
| Sep 26, 2026 | $249 |
| Sep 27, 2026 | $249 |
Google Flights price history returned through Scrapingdog for the dates and settings above. It is not a destination-wide average or a prediction. Source checked Sep 27, 2026.
Airport context and source-backed details to help you compare the whole journey.
San Diego, United States · Airport coordinates 32.734, -117.190
Lowest sample to SAN: $249 round trip from ORD, Dec 2–Dec 9. Different arrival airports may use different dates.
Airport informationThis page searches SAN — San Diego International Airport. Airport coverage follows the destination city market in the passenger dataset, with minor airports excluded. Always check the airport code on both legs: a city search can include different arrival airports, and the cheapest option may not be closest to where you are staying.
Read the sourceBTS recorded 702,445 scheduled passengers departing O’Hare and Midway for this destination city market from 2025-07 to 2026-06. That puts it at number 17 in our selected ranking. These are historical on-flight market passengers, not unique travelers, current flight frequencies or a measure of search popularity.
Read the sourceThe airport reference places San Diego International Airport in San Diego, United States, at 32.734°, -117.190°. Use the airport’s official information to plan your arrival and return journey. Our fare table compares air travel only; ground transfers, luggage and accommodation can change the total trip budget.
Read the sourceKeep an eye on the whole travel budget, from your first night to your last mile.
Compare places to stay in San Diego. Add your dates, check the location, and compare the final total and cancellation terms.
Explore San Diego stays ↗Booking.com · choose your travel datesPlanning a drive beyond San Diego? Compare rental cars, mileage, deposits and pickup hours. City-only trip? Public transit may suit you better.
Compare rental cars ↗Discover Cars · enter SAN and your datesThese are planning links, not priced offers. Hotel and car availability is checked by the provider. We currently receive no commission from these links.
Let us do the fare hunting. Our upcoming free newsletter will bring standout Chicago flight finds to your inbox, with travel dates and booking links so you can check the deal quickly. Use the signup panel near the top of this page when signup opens. It's free, and you'll be able to unsubscribe at any time.
The lowest seven-night round-trip search fare in our archive is $249, recorded Sep 27, 2026 for ORD to SAN, Dec 2–Dec 9, 2026. Our route archive starts Sep 27, 2026. This is our observed record, not an industry-wide all-time low, a verified booking price or a current offer.
Our lowest current seven-night sample is $249 round trip for one adult in economy, from ORD to SAN, Dec 2–Dec 9, 2026. It was checked Sep 27, 2026. This is a dated search result, not a guaranteed ticket price; confirm the return and full fare conditions before paying.
For the matched Dec 2–Dec 9, 2026 search, ORD had the lowest sample at $249. The highest and lowest airport fares were $48 apart. That applies to those dates and settings only. Try other matched dates and add your own ground transport cost in the airport calculator above.
The current sample includes a nonstop outbound from MDW to SAN on Dec 2, 2026, with a round-trip search fare of $297. Check the return direction separately: a nonstop outbound does not guarantee a nonstop return.
The travel-period chart compares only the dates we sampled. It cannot establish the cheapest month of the year. Start with a promising sampled period, then check nearby dates with the same trip length. The separate history chart tracks one specific search over time; it is not a travel calendar.
This destination market includes San Diego International Airport (SAN). Check the exact arrival code on the fare you choose, then compare the onward journey to your accommodation. The arrival section links airport information and our source-backed planning notes.
Not necessarily. The buttons open separate searches with matching airports and dates when a dated sample is available. Providers can show different airlines, sellers, baggage rules and live prices. The sampled Google Flights price is never a Skyscanner quote.
Do not assume bags are included unless the provider explicitly confirms them. Our research shows flight search fares; the accommodation and rental-car links are separate planning tools. Compare the final total, cancellation terms and location before booking any part of the trip.
Answers use the dated research and sources on this page. Read our flight-saving field notes for a broader planning checklist.
Get our best flight finds in your inbox ↗This page contains 284 current search-result observations across 26 airport/date searches. Route research is compiled by the Chicago Flight Research desk from the sources below.
Destination photography: photographer, source and reuse license. Airline logos identify the carriers shown in results; no partnership is implied.
BTS demand period: 2025-07 to 2026-06. Searches use one adult, economy, USD and the US market. We do not sell tickets, guarantee fares, or infer baggage inclusions. Read the full methodology
