- Must visit
Art Institute Of Chicago
One of the world’s leading art museums, famous for Impressionist masterpieces, American art, and major special exhibitions.
Flights from San Diego, CA to Chicago, IL depart on average 43 times per day, taking around 4h 33m. Cheap flight tickets for this journey start at $49 (€40) if you book in advance.
There are 9 flights per day. The earliest flight runs at 05:00, the last at 23:58. The fastest flight covers the 1729 miles (2784 km) distance in 3h 59m. December is the cheapest month to fly.
Distance 1729 miles (2784 km) |
Average flight duration 4h 33m |
Cheapest ticket price $49 (€40) |
Flights per day 43 |
Direct flights 9 |
Fastest flight 3h 59m |
First flight 5:00 AM |
Last flight 11:58 PM |
Cheapest Month Dec |
Cheapest Day Tue |
High Season Jul - Sep |
Low Season Oct - Dec |
Busiest Day Tue |
Least Busy Day Tue |
Best time to book 56 days |
Cheapest price
$93
Average price
$311
Fastest journey
4 h 12 m
Average duration
4 h 15 m
Flights per day
8
Distance
2784 km
The best way to find a cheap flight ticket from San Diego, CA to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from San Diego, CA to Chicago, IL will cost around $311 if you buy it on the day, but the cheapest tickets can be found for only $93.
Of the 8 flights that leave San Diego, CA for Chicago, IL onFri, Jul 10, 8 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Fri, Jul 10 the direct flights cover the 2784 km distance in an average of 4 h 15 m but if you time it right, some flights will get you there in just 4 h 12 m .
On Fri, Jul 10 the longest flights will take 4 h 17 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.










Omio recommends booking the train as it is the most popular option from San Diego, CA to Chicago, IL among Omio's users. If you are prioritising price take the flight with prices starting from $49. For those with little time consider booking a flight which can get you there in 4h 33m. In case you are seeking to minimise your carbon footprint the train is your best bet as it emits only 0.8 - 2.5kg. The ticket price range depends on the travel mode: a flight costs an average of $49, and a train costs an average of $196.
Distance: 1729 miles (2784 km)
| Flight | Most popular Train | Bus | Driving |
|---|---|---|---|
$318 Average price Cheapest | $451 Average price | $349 Average price | $428 Average price (fuel + tolls) |
7h 33m Average total duration Fastest 4h 33m Onboard + 3h 0m Additional time* | 49h 31m Average total duration 49h 1m Onboard + 30m Additional time* | 49h 18m Average total duration 48h 48m Onboard + 30m Additional time* | 30h 1m Average total duration (door-to-door) |
8.4 - 16.7kg CO2 emissions | 0.8 - 2.5kg CO2 emissions Lowest | 2.8 - 7.0kg CO2 emissions | - CO2 emissions |
![]() Most popular airline | ![]() Most popular train company | ![]() Most popular bus company | Your own car or car rental |
Direct Options | Direct Options | Direct Options | Direct Options |
Additional time: Average total travel duration to departure point, security checks and transfers.
This is compared to other travel options from San Diego, CA to Chicago, IL:
A flight is $31 (€25) less than a bus for this route with tickets for a bus from San Diego, CA to Chicago, IL costing on average $349 (€286).
A flight is $133 (€109) less than a train for this route with tickets for a train from San Diego, CA to Chicago, IL costing on average $451 (€370).
Other travel options to Chicago, IL take longer:
Bus takes on average 48h 48m.
Train takes on average 49h 1m.
The table below shows live departures for San Diego, CA to Chicago, IL flights for today, Thursday, July 9. You can also manually refresh the results below to see updated flight journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 5:52 PM San Diego, CA | 4h12 | 10:04 PM Chicago, IL | 0 transfersDirect | |
![]() | 8:03 PM San Diego, CA | 4h29 | 12:32 AM Chicago, IL | 0 transfersDirect | |
![]() | 9:32 PM San Diego, CA | 4h17 | 1:49 AM Chicago, IL | 0 transfersDirect | |
![]() | 10:09 PM San Diego, CA | 4h23 | 2:32 AM Chicago, IL | 0 transfersDirect | |
![]() | 10:19 PM San Diego, CA | 4h17 | 2:36 AM Chicago, IL | 0 transfersDirect | |
![]() | 11:32 PM San Diego, CA | 10h49 | 10:21 AM Chicago, IL | 0 transfersDirect | |
| Friday, July 10 | |||||
![]() | 1:20 PM San Diego, CA | 4h19 | 5:39 PM Chicago, IL | 0 transfersDirect | |
![]() | 1:21 PM San Diego, CA | 4h14 | 5:35 PM Chicago, IL | 0 transfersDirect | |
![]() | 2:00 PM San Diego, CA | 4h15 | 6:15 PM Chicago, IL | 0 transfersDirect | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
Compare train, bus, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
One of the world’s leading art museums, famous for Impressionist masterpieces, American art, and major special exhibitions.
A top natural history museum known for Sue the T. rex, ancient cultures, fossils, and broad science collections.
A large hands-on science museum with a German submarine, space exhibits, and interactive engineering displays.
Chicago’s signature downtown park, home to Cloud Gate, gardens, public art, and major seasonal events.
The city’s best-known avenue for architecture, shopping, and bustling urban energy along North Michigan Avenue.
A popular pedestrian waterfront with excellent skyline views, bridges, and easy access to boat architecture tours.
A thick, buttery crust pizza baked in a deep pan with layers of cheese, toppings, and chunky tomato sauce. It is one of Chicago’s most iconic and debated local specialties.
An all-beef hot dog on a poppy seed bun topped with yellow mustard, relish, onions, tomato, pickle spear, sport peppers, and celery salt. It is a classic local street food served without ketchup.
Thinly sliced seasoned roast beef piled onto an Italian roll, often dipped in its juices and topped with sweet peppers or giardiniera. It is a defining working-class Chicago sandwich.
Chicago’s world-famous fine-dining restaurant known for highly creative tasting menus and theatrical presentation. It offers one of the city’s most celebrated upscale dining experiences.
A beloved casual institution best known for breaded steak sandwiches and hearty Italian-American comfort food. It has a loyal local following and an old-school atmosphere.
A legendary Chicago chain celebrated for buttery-crust deep-dish pizza and a classic casual atmosphere. One of the city’s best-known places to try this signature dish.
Chicago is pricey for hotels and dining, but budget eats and public transit help keep daily costs manageable.
Tip 18-20% at restaurants; 15-20% for taxis and rideshares; USD 1-2 per drink at bars; USD 1-2 per bag for bellhops; USD 2-5 per night for housekeeping.
Find answers to the most common questions about traveling from San Diego, CA to Chicago, IL by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

Most San Diego, CA to Chicago, IL flights use the San Diego International Airport to O'Hare International Airport airport pair. Use this guide to compare San Diego, CA and Chicago, IL airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
San Diego International Airport is 4 km from San Diego city centre. Public transport options include:
San Diego International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food options include: Restaurants in terminals 1 and 2, including fast food and sit-down options like The Counter and Phil's BBQ
Free Wi-Fi available throughout the airport. ATMs are located in all terminals.
Lost and found is available at the station.
Available at San Diego International Airport: Parking, Taxis, WC.
Available at San Diego International Airport: Car Rental.
Accessibility facilities are available at San Diego International Airport: Elevators, ramps.
Nearby hotels include Hotels nearby, Sheraton San Diego Hotel & Mari within walking distance..
McClellan-Palomar Airport has practical services for this route, including Accessibility.
Accessibility facilities are available at McClellan-Palomar Airport: The place has an entrance that is wheelchair-accessible.
O'Hare International Airport is 3 km from Chicago city centre. Public transport options include:
O'Hare International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food options include: Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Free Wi-Fi available throughout the airport. ATMs are located throughout all terminals.
Lost and found is available at the station.
Available at O'Hare International Airport: Parking, Taxis, WC.
Available at O'Hare International Airport: Car Rental.
Accessibility facilities are available at O'Hare International Airport: Elevators, ramps, toilets.
Nearby hotels include Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby..
Here are some other resources that might have the information you need