Cheap flights from San Diego to Chicago

San Diego
SAN
Chicago FSS
CHI

Flight deals from San Diego to Chicago

Below you can see the best deals on flights San Diego — Chicago for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 15 September, from $85.

Top 10 cheap flights from San Diego to Chicago

F9
F9
$ 85

San Diego — Chicago

06:25—00:23
15 Sep 2026
15 h 58 m
1 stop
F9
F9
$ 88

San Diego — Chicago

16:54—00:23
15 Sep 2026
29 h 29 m
1 stop
F9
F9
$ 102

San Diego — Chicago

17:54—05:38
12 Sep 2026
9 h 44 m
1 stop
DL
F9
$ 108

San Diego — Chicago

15:45—05:38
12 Sep 2026
11 h 53 m
1 stop
F9
F9
F9
$ 110

San Diego — Chicago

10:28—05:38
10 Sep 2026
17 h 10 m
2 stops
F9
F9
$ 112

San Diego — Chicago

16:54—00:23
14 Sep 2026
29 h 29 m
1 stop
F9
F9
F9
$ 114

San Diego — Chicago

13:38—05:38
12 Sep 2026
14 h
2 stops
F9
F9
F9
$ 114

San Diego — Chicago

06:25—05:38
12 Sep 2026
21 h 13 m
2 stops
F9
F9
$ 115

San Diego — Chicago

16:54—00:23
13 Sep 2026
29 h 29 m
1 stop
F9
F9
$ 115

San Diego — Chicago

06:25—00:23
12 Sep 2026
15 h 58 m
1 stop

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the San Diego — Chicago flight

Looking for cheap flights from San Diego to Chicago? Compare fares from different airlines, check the flight schedule and travel time — and book your San Diego — Chicago ticket online at the best price.

The route has direct flights — around 243 flights per week, flights are operated by American Airlines, Hawaiian Airlines, Alaska Airlines, United Airlines and 2 more airlines, a nonstop flight takes about 4 h 11 min, the distance between the cities is around 2,792 km.

Planning your trip? You may find our Chicago travel guide, how to get from the airport into town and Chicago weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $85Min. price
SeptemberCheapest
MayPeak season
YesDirect flights
2,792 kmDistance
4 h 11 minTravel time
6Airlines
243 / wkFlights

Flight schedule from San Diego to Chicago

The table shows direct flights from San Diego to Chicago on the selected date. The flight takes approximately 4 h 11 min. Regular flights are operated by American Airlines, Hawaiian Airlines, Alaska Airlines and United Airlines. Departures from San Diego International Airport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

Today
Any time
Last update: 16 Aug 2026

Flight ticket prices by day: San Diego — Chicago

Below is a calendar of the lowest flight ticket prices for San Diego — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from $85 in September, and the most expensive are around $197 in May. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Average one-way fares from San Diego to Chicago by month. Tickets are usually cheapest in February (around $173) and priciest in July (about $262) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$179lowMay$221mediumSep$191low
Feb$173lowJun$244highOct$209medium
Mar$209mediumJul$262highNov$215medium
Apr$250highAug$250highDec$256high

Some values are estimated based on seasonality.

When to fly

Weather in Chicago: it is warmest in July (up to 27 °C on average) and coolest in January (around 0 °C). The driest month is November.

Tickets are usually cheapest in September and most expensive in May. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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How to get the best deal on a San Diego — Chicago ticket

  • Book ahead: fares for San Diego — Chicago are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • The cheapest month to fly to Chicago is usually September — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the San Diego — Chicago route are operated by 6 airlines; American Airlines runs the most flights (around 31% of all flights). Compare carriers, flight shares and schedules below.

  • American AirlinesAA
    25x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight SAN → ORD25x/week
      Duration
      4h 30m
      Days
      MTWTFSS
    30.9%Open →
  • Hawaiian AirlinesHA
    20x/week
    WebsiteFleet: 7511M pax/year
    • Direct flight SAN → ORD20x/week
    24.3%
  • Alaska AirlinesAS
    14x/week
    WebsiteFleet: 31545M pax/year
    • Direct flight SAN → ORD14x/week
      Duration
      4h 17m
      Days
      MTWTFSS
    17.3%Open →
  • United AirlinesUA
    14x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight SAN → ORD14x/week
      Duration
      4h 16m
      Days
      MTWTFSS
    16.9%Open →
  • Frontier AirlinesF9
    6x/week
    WebsiteFleet: 15329M pax/year
    • Direct flight SAN → ORD6x/week
    7.0%Open →
  • Qatar AirwaysQR
    3x/week
    WebsiteFleet: 26640M pax/year
    • Direct flight SAN → ORD3x/week
    3.7%Open →

Cities and airports on the San Diego — Chicago route

Flights San Diego — Chicago depart from San Diego International Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

San Diego

SAN
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the San Diego — Chicago flight

How long is the flight from San Diego to Chicago?

A nonstop San Diego — Chicago flight takes about 4 h 11 min — the distance between the cities is around 2,792 km.

How far is it from San Diego to Chicago?

The distance from San Diego to Chicago is about 2,792 km, which a nonstop flight covers in around 4 h 11 min.

Are there direct flights from San Diego to Chicago?

Yes, there are nonstop flights San Diego — Chicago — around 243 flights per week.

Which airlines fly from San Diego to Chicago?

Airlines operating San Diego — Chicago include American Airlines, Hawaiian Airlines, Alaska Airlines, United Airlines, Frontier Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do San Diego — Chicago flights use?

Flights from San Diego depart from San Diego International Airport, and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from San Diego to Chicago?

The price of a San Diego — Chicago ticket depends on your travel date, season and demand: it is usually cheapest to fly in September, and most expensive in May. Tickets typically cost between $85 and $197. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights San Diego — Chicago?

Flights San Diego — Chicago are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is September. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from San Diego to Chicago?

To catch a low fare San Diego — Chicago, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually September.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from San Diego

See all
San FranciscoSeattleLas VegasSan JosePhoenixDenverSacramentoNew York CityDallasSalt Lake CityAtlantaFresnoLos AngelesPortlandBostonHonoluluOrlandoAustinSanta RosaWashington, D.C.OaklandVancouverSan Jose del CaboBoiseRedmondRenoMinneapolisCharlotteKahuluiSan Luis ObispoHoustonEugeneDetroitMiamiTorontoMontrealMontereyFort LauderdaleKailua-KonaTampa

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverNashvilleLondonIndianapolisMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityPhoenixMiamiLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochesterCleveland

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