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Cheap Flights from San Diego (SAN) to Chicago (CHIA)

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Compare San Diego International to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

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Flight deals from San Diego International to Chicago

Looking for a cheap last-minute deal or the best return flight from San Diego International to Chicago? Find the lowest prices on one-way and return tickets right here.
Chicago.$181 per passenger.Departing Tue, 5 Aug, returning Tue, 12 Aug.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from San Diego International on Tue, 5 Aug, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Tue, 12 Aug, arriving in San Diego International.Price includes taxes and charges.From $181, select.
Chicago.$181 per passenger.Departing Sat, 28 Jun, returning Wed, 2 Jul.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from San Diego International on Sat, 28 Jun, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Wed, 2 Jul, arriving in San Diego International.Price includes taxes and charges.From $181, select.
Chicago.$181 per passenger.Departing Sat, 12 Jul, returning Sat, 19 Jul.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from San Diego International on Sat, 12 Jul, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Sat, 19 Jul, arriving in San Diego International.Price includes taxes and charges.From $181, select.
Chicago.$228 per passenger.Departing Thu, 6 Nov, returning Mon, 10 Nov.Return flight with Hawaiian Airlines.Outbound direct flight with Hawaiian Airlines departs from San Diego International on Thu, 6 Nov, arriving in Chicago O'Hare International.Inbound direct flight with Hawaiian Airlines departs from Chicago O'Hare International on Mon, 10 Nov, arriving in San Diego International.Price includes taxes and charges.From $228, select.
Chicago.$246 per passenger.Departing Wed, 1 Oct, returning Wed, 8 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Wed, 1 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 8 Oct, arriving in San Diego International.Price includes taxes and charges.From $246, select.
Chicago.$248 per passenger.Departing Sat, 30 Aug, returning Wed, 3 Sep.Return flight with United.Outbound direct flight with United departs from San Diego International on Sat, 30 Aug, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Wed, 3 Sep, arriving in San Diego International.Price includes taxes and charges.From $248, select.
Chicago.$249 per passenger.Departing Tue, 9 Sep, returning Tue, 23 Sep.Return flight with United.Outbound direct flight with United departs from San Diego International on Tue, 9 Sep, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 23 Sep, arriving in San Diego International.Price includes taxes and charges.From $249, select.
Chicago.$251 per passenger.Departing Sat, 28 Jun, returning Mon, 30 Jun.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from San Diego International on Sat, 28 Jun, arriving in Chicago O'Hare International.Inbound direct flight with Frontier Airlines departs from Chicago O'Hare International on Mon, 30 Jun, arriving in San Diego International.Price includes taxes and charges.From $251, select.

Find the cheapest month to fly from San Diego International to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like San Diego International to Chicago flights are currently cheapest in July.
Jun
from $251
Jul
from $181
Aug
from $181
Sep
from $249
Oct
from $246
Nov
from $228
Dec
from $562
Jan
from $601
Feb
from $633
Mar
from $568
Apr
from $598
May
Find prices

Direct flights from San Diego International to Chicago

Alternative San Diego International to Chicago routes

Looking for the cheapest, fastest or easiest route from San Diego International to Chicago? You could fly into the following airports instead.

San Diego to Chicago: Flight information

The things to know before you go.
Cheapest flight found$181
Cheapest month to flyJune
Average flight time4 hrs, 9 mins
Most popular airlineAlaska Airlines
Average flights per week279

Finding cheap flights from San Diego International to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from San Diego International to Chicago is $181. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
4 hours and 8 minutes is the average flight time from San Diego International to Chicago.
Alaska Airlines, Southwest Airlines and American Airlines fly direct from San Diego International to Chicago.
As of June 2025, there are 279 flights per week flying from San Diego International to Chicago.
The cheapest month to fly from San Diego International to Chicago is usually June.
If you're flying from San Diego International Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $181.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from San Diego International Airport to Chicago on Saturday, 28 June 2025.
Yes – the average flight time is 4 hours and 8 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In June, the average temperature is usually around 19°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Frontier Airlines offers the cheapest flight tickets to Chicago.

Flying from San Diego International Airport (SAN) to Chicago: what you need to know

  • The average length of a direct flight from San Diego International Airport to Chicago is 4 hours 25 minutes.

  • The timezone in Chicago is UTC-5. The city is two hours ahead of San Diego, where San Diego International Airport is located.

  • With 58 flights a week between the two airports, San Diego International Airport (SAN) to O'Hare International Airport (ORD) is the most popular route. American Airlines operates the earliest flight at 06:15. If you prefer to get more out of your day before flying, the latest departure from SAN to ORD is with American Airlines at 22:50.

  • To avoid missing your SAN to Chicago flight, allow plenty of time for things like check-in and baggage drop. Arriving two hours ahead of international departures and one hour before domestic flights is the standard rule.

  • If you're travelling during a major holiday or another peak period, give yourself more time. A good rule is two hours before domestic flights and up to four hours before international departures. Queues at check-in and security will be longer.

  • Direct San Diego International Airport to Chicago tickets are available for booking. O'Hare International Airport (ORD) is where you'll complete your journey.

  • You'll have your pick of carriers that offer direct flights from San Diego International Airport to Chicago. Get on board with any of these:

  • SAN is about 3 kilometres from central San Diego. If you're driving, ride-sharing or catching a cab from the centre, it'll take you 10 minutes or so to get there, depending on the traffic. If you're using public transport, expect the travel time to be around 20 minutes.

  • Searching for a hotel near SAN? If you've booked an early flight from San Diego International Airport to Chicago, these stays will put you moments from your departure gate:

  • Of the departures from San Diego International Airport, 71.38% arrive on time at their destination.

  • You'll find SAN at N Harbour Dr.

How to find the cheapest flights from San Diego International Airport (SAN) to Chicago

  • The best price we've seen for a one-way San Diego International Airport to Chicago flight is $74. The cheapest price for a return flight is $181. Remember fares may change due to demand at the time of booking.

  • Lock in cheap flights from SAN to Chicago by booking one month ahead. According to our research, that's the best time for landing a bargain.

  • The best month for scoring cheap San Diego International Airport to Chicago tickets is May. Use the 'Whole month' tool to compare all available prices, then select the dates with the lowest fares.

  • Finding a cheap flight from SAN to Chicago is a breeze with Price Alerts. Simply set up one of these automatic notifications and we'll get in touch when a lower fare pops up.

  • Save money on your flight from San Diego International Airport to Chicago with the help of our filters. Choose your ideal duration, number of stops and airlines, then sort the results by 'Cheapest' for the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to the centre of Chicago takes around 35 minutes to reach by car. The centre is roughly 40 kilometres away.

  • It typically takes 55 minutes if you're using public transport.

  • Think about booking a hotel close to ORD if you're coming in on a late flight from San Diego International Airport to Chicago. Choose one of these options and make your first night all about catching up on rest:

  • Pick up an O'Hare International Airport rental car and explore Chicago and beyond with your own set of wheels. Routes Car Rentals, Dollar and Budget are leading providers you can book with here.

  • To get the lowest price, book your vehicle from O'Hare International Airport around four weeks ahead of your flight from SAN to Chicago.

  • The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Central Chicago is around 19 kilometres from Chicago Midway International Airport (MDW). Once your flight from San Diego International Airport to Chicago has landed and you've made your way out of the airport, expect a drive of about 20 minutes.

  • The journey will take roughly 45 minutes on public transport.

  • You'll find some comfortable places to park your luggage (and yourself) near MDW. Settle in and get cosy after your SAN to Chicago flight at any of these perfectly located options:

  • Forget about public transport schedules or long cab queues. Grab a Chicago Midway International Airport rental car and let your trip unfold on your terms. Compare availability and rates from Dollar, Hertz and Budget.

  • Get the pick of the lot. Reserving your ride from MDW four weeks in advance often means more savings and a greater selection of vehicles.

  • Chicago Midway International Airport can be found at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Step off your flight from San Diego International Airport to Chicago and head for your hotel or jump right into sightseeing. The centre of Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and typically takes 1 hour 25 minutes to drive there.

  • Public transport will take you there in around 4 hours 15 minutes.

  • Stay at a hotel near RFD and go from the runway to resting in a snap. Whether you have a late SAN to Chicago flight or just want to simplify your travel plans, these stays will have you settling in quickly:

  • Begin your journey without stressing over how to arrive at your destination with a Chicago Rockford International Airport rental car. Find your perfect set of wheels with reliable suppliers here like Budget, Alamo and National.

  • Rental providers sometimes offer promotions for early bookings, so secure your ride from RFD a few weeks in advance of your flight from San Diego International Airport to Chicago. A bit of planning goes a long way for your wallet.

  • Chicago Rockford International Airport can be found at 2 Airport Cir.

Best time to go to Chicago

  • Visit Chicago in peak season if you want a bustling atmosphere, but remember that hotel prices may be higher. Alternatively, book flights from San Diego International Airport to Chicago in the low season when prices are cheaper and it's quieter.

  • Lock in a San Diego International Airport to Chicago flight ticket with a departure in July to explore the city during its warmest month. Expect temperatures to range from 15ºC (59ºF) to 29ºC (84ºF).

  • Search for cheap tickets from SAN to Chicago in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

  • When it comes to looking for somewhere to lay your head, you'll find the best stays in Chicago right here. Check out these options once you've booked your flight from San Diego International Airport to Chicago:

  • There are so many things to explore in this city it can be tricky to know where to start. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are leading attractions which should feature on any well-planned Chicago itinerary.

Explore more of United States

  • Chicago has its own special appeal, but there are so many other corners of United States waiting to be discovered. About 451 kilometres south-east of Chicago, a visit to Columbus will keep your itinerary busy. Start with attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another favourite destination in United States and is around 257 kilometres south-east of Chicago. No trip is complete without dropping by The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from San Diego to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.