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

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Compare San Diego to Chicago flight deals

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Flight deals from San Diego to Chicago

Looking for a cheap last-minute deal or the best return flight from San Diego 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.$226 per passenger.Departing Tue, 9 Sep, returning Tue, 23 Sep.Return flight with Spirit Airlines.Outbound indirect flight with Spirit Airlines, departs from San Diego International on Tue, 9 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Tue, 23 Sep, arriving in San Diego International.Price includes taxes and charges.From $226, select.
Chicago.$244 per passenger.Departing Tue, 29 Jul, returning Tue, 5 Aug.Return flight with Spirit Airlines and Frontier Airlines.Outbound indirect flight with Spirit Airlines, departs from San Diego International on Tue, 29 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 5 Aug, arriving in San Diego International.Price includes taxes and charges.From $244, select.
Chicago.$247 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 $247, select.
Chicago.$248 per passenger.Departing Sat, 13 Sep, returning Tue, 16 Sep.Return flight with United.Outbound direct flight with United departs from San Diego International on Sat, 13 Sep, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 16 Sep, arriving in San Diego International.Price includes taxes and charges.From $248, 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.

Find the cheapest month to fly from San Diego to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like San Diego to Chicago flights are currently cheapest in July.
Jun
from $251
Jul
from $181
Aug
from $181
Sep
from $226
Oct
from $247
Nov
from $266
Dec
from $563
Jan
from $596
Feb
Find prices
Mar
from $569
Apr
from $596
May
Find prices

Direct flights from San Diego to Chicago

Alternative San Diego to Chicago routes

Looking for the cheapest, fastest or easiest route from San Diego 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, 8 mins
Most popular airlineAlaska Airlines
Average flights per week289

Finding cheap flights from San Diego 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 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 to Chicago.
Alaska Airlines, Southwest Airlines and American Airlines fly direct from San Diego to Chicago.
As of June 2025, there are 289 flights per week flying from San Diego to Chicago.
The cheapest month to fly from San Diego to Chicago is usually June 2025.
If you're flying from San Diego, 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 is currently cheapest to fly from San Diego 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.
The cheapest airline that flies to Chicago is Frontier Airlines .

Travelling from San Diego to Chicago: what you need to know

  • Countless great adventures start at one of San Diego's main airports, San Diego International Airport (SAN) or McClellan-Palomar Airport (CLD). Explore your options for booking a flight from San Diego to Chicago setting off from either of these.

  • O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the primary entry points to Chicago.

  • Hop on a direct San Diego to Chicago flight and you'll be travelling for an average of 4 hours 5 minutes.

  • Chicago is two hours ahead of San Diego and observes the UTC-5 timezone.

  • San Diego International Airport (SAN) to O'Hare International Airport (ORD) is the most popular route that connects these two cities. There are 58 departures a week to choose from. If you prefer starting your day later, the last flight from San Diego to Chicago is with American Airlines at 22:59. Go for the first SAN to ORD departure with United Airlines at 06:15 to make the most of your arrival in Chicago.

  • Give yourself plenty of time to make your San Diego to Chicago flight. As a general rule, turn up at least two hours before international departures and an hour ahead for domestic flights.

  • Popular months like July or high seasons such as Christmas and New Year will mean longer waits at security and check-in. Play it safe and get to the terminal even earlier. Arriving two hours before domestic flights and four hours ahead of international departures is a smart move.

How to find the cheapest flights from San Diego to Chicago

  • $81 is the best price for a one-way ticket from San Diego to Chicago. A return flight starts at $181. These fares can change depending on demand and availability.

  • To snag cheap San Diego to Chicago flights, book your journey two months before your departure.

  • Plan your trip for May. That's the best month for landing a great bargain on plane tickets from San Diego to Chicago. If you're flexible with your travel dates, use the 'Whole month' tool to see the cheapest price across every month.

  • You don't need to search every day to see if fares have dropped when you set up a Price Alert. We'll update you as soon as a better deal comes up on cheap flights from San Diego to Chicago.

  • Find a cheap San Diego to Chicago flight with the help of our filters. Choose your preferred duration, departure time and airlines, then sort the results by 'Cheapest' to see the best deals.

Flying from San Diego

San Diego International Airport (SAN)

  • Start your trip at San Diego International Airport (SAN), which offers multiple direct flights from San Diego to Chicago. From SAN, you can fly seamlessly to O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW).

  • You'll have your pick of airlines that offer direct San Diego to Chicago plane tickets out of SAN. Claim your seat with one of these carriers:

  • Located around 3 kilometres from central San Diego, SAN can be reached in about 10 minutes by car (depending on traffic). The journey on public transport is roughly 20 minutes.

  • Booked an early flight from San Diego to Chicago? Avoid the last-minute rush to the airport (and catch some extra z's) by choosing one of these stays close to San Diego International Airport:

  • Of all flights leaving San Diego International Airport, 71.38% arrive on time at their destination.

  • SAN's address is N Harbour Dr.

Arriving in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 26 kilometres. It takes around 35 minutes to get to the centre driving.

  • If you're travelling by public transport, expect a journey time of about 55 minutes.

  • Consider staying in a hotel near ORD if you have a late flight from San Diego to Chicago. Select one of these options and avoid the hassle of a long transfer:

  • Travel at your own pace with an O'Hare International Airport rental car. Pick up a set of wheels from Routes Car Rentals, Dollar or Budget and discover more of Chicago and beyond.

  • To get the lowest price, reserve your vehicle from O'Hare International Airport about four weeks in advance of your San Diego to Chicago flight.

  • ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Central Chicago is approximately 14 kilometres from Chicago Midway International Airport (MDW). After your flight from San Diego to Chicago has touched down and you've made your way to arrivals, expect a drive of around 20 minutes.

  • If you're catching public transport, it'll take about 45 minutes.

  • Hang the 'Do not disturb' sign on your door and unwind at a hotel near MDW. Here are a few options where you can settle in after your flight from San Diego to Chicago:

  • The fastest way to reach your destination is with a Chicago Midway International Airport rental car. Grab your wheels from Dollar, Hertz or Budget and make a speedy getaway.

  • Get what you want, not just what's left over. Securing your ride from MDW four weeks in advance often means lower prices and a greater range of vehicles.

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

Chicago Rockford International Airport (RFD)

  • Set off for the city centre after your flight from San Diego to Chicago has landed. Central Chicago is around 129 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 25 minutes to get to by car.

  • The journey will take you roughly 4 hours 15 minutes by public transport.

  • Put yourself in the driver's seat of the next chapter of your journey with a Chicago Rockford International Airport rental car. Budget, Alamo and National are dependable companies for booking.

  • If you're hoping for a specific type of vehicle, booking early increases your chances of getting what you want. Secure your ride from RFD a few weeks ahead of your flight from San Diego to Chicago.

  • Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

  • It's time to choose your dates for your flight from San Diego to Chicago. August is the busiest month to travel to Chicago. If you prefer a more relaxed atmosphere, go in January.

  • When booking your San Diego to Chicago tickets, consider the type of weather you enjoy. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • Look for cheap flights from San Diego 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

Explore more of United States

  • You've done Chicago, now it's time to explore other parts of United States. Journey around 451 kilometres south-east to Columbus to tick off its leading attractions. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, there's plenty to keep you busy.

  • If there's time to check out another corner of United States, head for Indianapolis, roughly 257 kilometres south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are among its highlights.

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.