Cheap flights from San Diego to Chicago

Flights overview

Useful information for finding cheap flights from San Diego to Chicago and booking your next trip
Cheapest round-trip flights $156
Southwest Nonstop 4 hr Sat, Feb 28 — Sat, Mar 7
The cheapest round-trip flight from San Diego to Chicago is currently $156
Cheapest one-way flight $66
Southwest Nonstop 4 hr Sat, Apr 25
The cheapest one-way flight from San Diego to Chicago is currently $66
Last-minute weekend getaway $222
Frontier 1 stop 23 hr Sat, Jan 31 — Mon, Feb 2
The cheapest last-minute weekend getaway from San Diego to Chicago is currently $222
Cheapest business class flights $727
Alaska Nonstop 5 hr Thu, Apr 23 — Thu, Apr 30
The cheapest business class round-trip flight from San Diego to Chicago is currently $727
Fastest flight 3 hr 50 min The fastest nonstop flight from San Diego to Chicago takes 3 hr 50 min
Nonstop flights Every day There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from San Diego to Chicago is typically September. The most expensive month to fly is typically May.
September
Cheapest
Typical prices: $130–190
May
Most expensive
Typical prices: $180–260

Popular airlines from San Diego to Chicago

  • Southwest
    Nonstop
    from $140
    Typical price: $195–475
    14 weekly nonstop flights
    SAN - MDW Every day
    2467 weekly connecting flights
    SAN - MDW, ORD Every day
  • United
    Nonstop
    from $157
    Typical price: $180–465
    25 weekly nonstop flights
    SAN - ORD Every day
    436 weekly connecting flights
    SAN - ORD Every day
  • American
    Nonstop
    from $157
    Typical price: $180–495
    14 weekly nonstop flights
    SAN - ORD Every day
    348 weekly connecting flights
    SAN - ORD Every day
  • Alaska
    Nonstop
    from $167
    Typical price: $195–570
    14 weekly nonstop flights
    SAN - ORD Every day
    16 weekly connecting flights
    SAN - ORD Every day
  • Delta
    from $237
    Typical price: $255–610
    349 weekly connecting flights
    SAN - MDW, ORD Every day
  • Frontier
    from $180
    Typical price: $155–345
    36 weekly connecting flights
    SAN - MDW, ORD Every day

Popular airports near San Diego

  • San Diego International Airport (SAN)
    San Diego United States 10 min 2 mi
  • Tijuana International Airport (TIJ)
    Tijuana Mexico 37 min 16 mi
  • Los Angeles International Airport (LAX)
    Los Angeles United States 2 hr 2 min 111 mi
  • John Wayne Airport (SNA)
    Santa Ana United States 1 hr 21 min 78 mi

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 27 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 24 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from San Diego to Chicago

The cheapest flights from San Diego to Chicago are usually in September. Typical ticket prices in September range from $130 to $190.
The cheapest round-trip flight from San Diego to Chicago recently found on Google Flights was with Southwest from $156. The cheapest one-way flight was with Southwest from $66.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from San Diego to Chicago is $140, flying from Apr 18 to Apr 25.
  • The cheapest United flight from San Diego to Chicago is $157, flying from Apr 18 to Apr 25.
  • The cheapest American flight from San Diego to Chicago is $157, flying from Feb 28 to Mar 7.
  • The cheapest Alaska flight from San Diego to Chicago is $167, flying from Mar 2 to Mar 10.
  • The cheapest Delta flight from San Diego to Chicago is $237, flying from Apr 16 to Apr 22.
  • The cheapest Frontier flight from San Diego to Chicago is $180, flying from Apr 16 to Apr 22.
The cheapest round-trip flight from San Diego to Chicago starts at $156 from Sat, Feb 28 to Sat, Mar 7. The cheapest one-way flight starts at $66 and departs on Sat, Apr 25.
3 hr 50 min is the shortest flight time from San Diego to Chicago.
Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.
It's easy to use Google Flights to find the cheapest days to fly from San Diego to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from San Diego to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from San Diego to Chicago.

In terms of nonstop flights, United is the most popular. United offers 25 nonstop flights and 436 connecting flights per week. United flies from San Diego International Airport (SAN) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Southwest is the most popular. Southwest offers 14 nonstop flights and 2,467 connecting flights per week. Southwest flies from San Diego International Airport (SAN) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from San Diego to Chicago are:
  • American offers 14 nonstop flights and 348 connecting flights per week. American flies from San Diego International Airport (SAN) to Chicago O'Hare International Airport (ORD) .
  • Alaska offers 14 nonstop flights and 16 connecting flights per week. Alaska flies from San Diego International Airport (SAN) to Chicago O'Hare International Airport (ORD) .
  • Delta offers 349 connecting flights per week. Delta flies from San Diego International Airport (SAN) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
  • Frontier offers 36 connecting flights per week. Frontier flies from San Diego International Airport (SAN) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
The number of connecting flights refers to distinct flights with at least one stop between San Diego and Chicago.
The cheapest round-trip flight from San Diego to Chicago recently found on Google Flights was with Southwest from $156. The cheapest one-way flight was with Southwest from $66.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from San Diego to Chicago is $140, flying from Apr 18 to Apr 25.
  • The cheapest United flight from San Diego to Chicago is $157, flying from Apr 18 to Apr 25.
  • The cheapest American flight from San Diego to Chicago is $157, flying from Feb 28 to Mar 7.
  • The cheapest Alaska flight from San Diego to Chicago is $167, flying from Mar 2 to Mar 10.
  • The cheapest Delta flight from San Diego to Chicago is $237, flying from Apr 16 to Apr 22.
  • The cheapest Frontier flight from San Diego to Chicago is $180, flying from Apr 16 to Apr 22.
Southwest, United, American and Alaska fly direct from San Diego to Chicago.
  • There are 14 Southwest direct flights from San Diego to Chicago per week. Flights are available every day.
  • There are 25 United direct flights from San Diego to Chicago per week. Flights are available every day.
  • There are 14 American direct flights from San Diego to Chicago per week. Flights are available every day.
  • There are 14 Alaska direct flights from San Diego to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
The cheapest last-minute deal between San Diego and Chicago at price $222 is offered by Frontier from Sat, Jan 31 to Mon, Feb 2.
Southwest, United, American and Alaska fly direct from San Diego to Chicago.
  • There are 14 Southwest direct flights from San Diego to Chicago per week. Flights are available every day.
  • There are 25 United direct flights from San Diego to Chicago per week. Flights are available every day.
  • There are 14 American direct flights from San Diego to Chicago per week. Flights are available every day.
  • There are 14 Alaska direct flights from San Diego to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
There are direct flights from San Diego to Chicago on a daily basis.
The cheapest direct (nonstop) round-trip flights between San Diego and Chicago start at $156 from Sat, Feb 28 to Sat, Mar 7 with Southwest.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from San Diego to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between San Diego and Chicago start at $727 from Thu, Apr 23 to Thu, Apr 30 with Alaska.
The cheapest economy class round-trip flights between San Diego and Chicago start at $156 from Sat, Feb 28 to Sat, Mar 7.
To book business class trips from San Diego to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between San Diego and Chicago starts at $222 from Sat, Jan 31 to Mon, Feb 2 with Frontier.
The cheapest last-minute deal between San Diego and Chicago at price $222 is offered by Frontier from Sat, Jan 31 to Mon, Feb 2.
To find last-minute flight deals from San Diego to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

Search more flights

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