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Flights San Diego — Chicago

San Diego
SAN
Chicago
CHI

Cheap flights San Diego — 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 25 August, from AED 399.

Top 10 cheap flights San Diego — Chicago

Direct flights San Diego — Chicago

Direct flight options for San Diego — Chicago with no stopovers on upcoming dates. A direct flight is faster and more convenient — especially when travelling with luggage or children.

The fastest direct flight is operated by United Airlines — travel time is 4 h 11 min.

Top 10 direct flights San Diego — Chicago

About the San Diego — Chicago flight

On this page, you can book flights from San Diego to Chicago. The distance between the cities is 2,792 km, with approximately 81 flights per week. To help plan your trip, check out our guides on getting to the airport for departure and airport transfer options upon arrival.

Flights on this route are operated by United Airlines, American Airlines, and Alaska Airlines. Since fares are dynamic, we recommend using the low-price calendar and price trend chart to find the best time to buy your tickets.

Flight schedule San Diego — Chicago

The table shows direct flights San Diego → 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.

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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 AED 358 in F, and the most expensive are around AED 682 in u. 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

San Diego → Chicago, average one-way price

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
JanAED 709lowMayAED 874mediumSepAED 756low
FebAED 685lowJunAED 968highOctAED 827medium
MarAED 827mediumJulAED 1,039highNovAED 850medium
AprAED 992highAugAED 992highDecAED 1,016high

Some values are estimated based on seasonality.

When to fly

According to climate data, the warmest time to visit Chicago is July, with an average temperature of 26.5°C. The lowest temperatures occur in January, while rainfall peaks in May, with up to 126 mm of precipitation recorded monthly.

If you're looking to save, September is considered the most budget-friendly month to fly, with fares starting AED 358. The highest rates are typically found in April, reaching AED 682.

The best time for a trip is September: you'll enjoy a comfortable temperature of around 23.5°C along with the lowest flight prices. If your goal is to save as much as possible, try to avoid booking for travel in April.

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

  • Start monitoring prices 4–6 weeks before departure to secure the best fares.
  • Tuesday and Wednesday are often the cheapest days to fly from San Diego, while flights on Fridays and Sundays tend to be more expensive.
  • When choosing Frontier Airlines or other low-cost carriers, check the baggage policy carefully, as extra fees can significantly increase the total cost.
  • Use the low-price calendar on this page to find flights AED 358 for nearby dates.

Airlines

Six airlines operate on the route from San Diego to Chicago, including major carriers like United Airlines and American Airlines. With a total of about 81 flights per week, there is a wide variety of departure times for both direct flights and connecting options. Below you'll find a detailed schedule and information for each carrier to help you plan your trip.

  • American Airlines
    American AirlinesAA
    25x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight SAN → ORD25x/week
      Duration
      4h 26m
      Days
      MTWTFSS
    30.9%Open →
  • Hawaiian Airlines
    Hawaiian AirlinesHA
    20x/week
    WebsiteFleet: 7511M pax/year
    • Direct flight SAN → ORD20x/week
    24.3%Open →
  • Alaska Airlines
    Alaska AirlinesAS
    14x/week
    WebsiteFleet: 31545M pax/year
    • Direct flight SAN → ORD14x/week
      Duration
      4h 17m
      Days
      MTWTFSS
    17.3%Open →
  • United Airlines
    United AirlinesUA
    14x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight SAN → ORD14x/week
      Duration
      4h 18m
      Days
      MTWTFSS
    16.9%Open →
  • Frontier Airlines
    Frontier AirlinesF9
    6x/week
    WebsiteFleet: 15329M pax/year
    • Direct flight SAN → ORD6x/week
    7.0%Open →
  • Qatar Airways
    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 direct flight covering 2,792 km takes an average of 3 hours and 30 minutes. Travel time may vary slightly depending on the airline and weather conditions.

Which airlines fly this route?

Six carriers operate regular flights, including United Airlines, American Airlines, Alaska Airlines, and Frontier. You can compare their options in the list above.

Are there direct flights from San Diego to Chicago?

Yes, there are many direct flights available on this route, allowing you to reach your destination without any layovers.

How can I find the cheapest flight?

Ticket prices fluctuate constantly based on demand. You can always check the current lowest price for your dates using the low-price calendar on this page.

Which airport does the flight arrive at in Chicago?

Most flights from San Diego arrive at the main airports in Chicago. You will see specific information about the arrival terminal when selecting your ticket.

Where else you can fly from San Diego

San FranciscoSeattleLas VegasNew York CityAtlantaLos AngelesBostonHonoluluWashington, D.C.Amsterdam

Where else you can fly from Chicago

New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverNashvilleLondonIndianapolisMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochesterCleveland
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