Travelling from San Diego to Chicago: what you need to know
Begin planning your trip by checking out the ideal departure point for your flight from San Diego to Chicago. Explore your options for leaving from San Diego International Airport (SAN) or McClellan-Palomar Airport (CLD), two of the city's main airports.
The major gateways to Chicago are O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW).
The average length of a direct San Diego to Chicago flight is 4 hours 5 minutes.
The timezone in Chicago is UTC-5, which is two hours ahead of San Diego.
San Diego International Airport (SAN) to O'Hare International Airport (ORD) is the most traveled route between these two cities. There are 58 weekly departures to choose from. If you have things to finalize before heading off, the last flight from San Diego to Chicago is with American Airlines at 22:50. Opt for the first SAN to ORD departure operated by American Airlines at 06:15 to make the most of your arrival in Chicago.
Allow plenty of time to get on 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.
Be prepared for longer queues in popular months such as July. Arriving up to four hours ahead of an international flight and two hours for domestic departures is a wise move.
How to find the cheapest flights from San Diego to Chicago
₹ 5,905 is the best price for a one-way ticket from San Diego to Chicago. A return flight starts at ₹ 10,841. 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 journey at San Diego International Airport (SAN), which has a range of direct flights from San Diego to Chicago. From SAN, you can fly straight into O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW).
Well-known airlines that offer direct San Diego to Chicago plane tickets departing from SAN include:
The journey from central San Diego to SAN takes about 20 minutes on public transport. If you drive, ride-share or grab a cab, you'll cover the 3 kilometres in 10 minutes or so, depending on traffic conditions.
Have an early flight from San Diego to Chicago? Avoid the stress of rushing to the airport (and sneak in some extra precious sleep) by choosing one of these hotels close to San Diego International Airport:
Of all flights departing from San Diego International Airport, 71.38% touch down on time at their destination.
You'll find SAN at N Harbour Dr.
Arriving in Chicago
O'Hare International Airport (ORD)
O'Hare International Airport (ORD) is approximately 26 kilometres from central Chicago. If you're catching a cab or a ride-share, the drive will take around 35 minutes.
Getting there on public transport will take you around 55 minutes.
The last thing you need is a long journey to your hotel if you're landing late on a flight from San Diego to Chicago. Check in to one of these accommodation options near ORD instead:
Follow your own route with an O'Hare International Airport rental car. Pick up your wheels from Routes Car Rentals, Dollar or Budget and experience more of Chicago and beyond.
Lock in the best rate by booking your vehicle from O'Hare International Airport about four weeks ahead of your trip.
ORD is situated at 10000 West O'Hare.
Chicago Midway International Airport (MDW)
Chicago Midway International Airport (MDW) is around 14 kilometres from the centre of Chicago. Once you've hopped off your flight from San Diego to Chicago, it'll take you approximately 20 minutes to reach the heart of the city in a ride-share or cab.
You can expect the trip to take about 45 minutes on public transport.
You'll find some great places to call home for the night near MDW. Settle in and get cosy after your San Diego to Chicago flight at one of these perfectly located options:
Dollar, Hertz and Budget make collecting a Chicago Midway International Airport rental car easy and quick. These providers are located in or around the terminal and will have you behind the wheel before you know it.
Avoid potential price surges. Securing your ride four weeks before your arrival at MDW will save you money.
You'll find Chicago Midway International Airport at 5700 South Cicero.
Chicago Rockford International Airport (RFD)
Chicago Rockford International Airport (RFD) is about 129 kilometres from central Chicago. It takes about 1 hour 25 minutes to get to the city centre in a car after your flight from San Diego to Chicago.
Public transport can get you there in roughly 4 hours 15 minutes.
Whether you're looking for a budget-friendly compact for a solo adventure or a full-size SUV to transport your group, you'll find the perfect Chicago Rockford International Airport rental car for your needs. Check out wheels available here from providers such as Budget, Alamo and National.
Booking a couple of weeks in advance of your flight from San Diego to Chicago is a good move. Along with more affordable prices, you'll be able to choose the vehicle make and model you prefer at RFD.
Chicago Rockford International Airport can be found 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 to 29ºC.
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 and 3ºC on average.
More about Chicago
Start your Chicago trip off on the right foot by choosing the perfect place to stay. After booking your flight from San Diego to Chicago, explore our range of hotels including:
There are so many things to explore in this city it can be tricky to work out where to begin. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are popular attractions which should be on every Chicago itinerary.
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.
