- Must visit
Art Institute of Chicago
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
Flights from San Diego, CA to Chicago, IL depart on average 48 times per day, taking around 4h 25m. Cheap flight tickets for this journey start at lei572 but you can travel from only lei534 by bus.
There are 10 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 4h 9m. December is the cheapest month to fly.
Distance 1729 miles (2784 km) |
Average flight duration 4h 25m |
Cheapest ticket price lei572 |
Flights per day 48 |
Direct flights 10 |
Fastest flight 4h 9m |
First flight 5:00 AM |
Last flight 11:58 PM |
Cheapest Month Dec |
Cheapest Day Tue |
High Season Jan - Mar |
Low Season Oct - Dec |
Busiest Day Tue |
Least Busy Day Tue |
Best time to book 56 days |
Cheapest price
lei225
Average price
lei1270
Fastest journey
4 h 4 m
Average duration
5 h 3 m
Flights per day
5
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 lei1270 if you buy it on the day, but the cheapest tickets can be found for only lei225.
Of the 5 flights that leave San Diego, CA for Chicago, IL onTue, Aug 25, 5 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Tue, Aug 25 the direct flights cover the 2784 km distance in an average of 5 h 3 m but if you time it right, some flights will get you there in just 4 h 4 m .
On Tue, Aug 25 the longest flights will take 8 h 29 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 lei572. For those with little time consider booking a flight which can get you there in 4h 25m. 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 lei572, and a train costs an average of lei897.
Distance: 1729 miles (2784 km)
| Flight | Most popular Train | Bus | Driving |
|---|---|---|---|
lei938 Average price Cheapest | lei1579 Average price | lei948 Average price | lei1991 Average price (fuel + tolls) |
7h 25m Average total duration Fastest 4h 25m Onboard + 3h 0m Additional time* | 49h 48m Average total duration 49h 18m 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 lei10 less than a bus for this route with tickets for a bus from San Diego, CA to Chicago, IL costing on average lei948.
A flight is lei642 less than a train for this route with tickets for a train from San Diego, CA to Chicago, IL costing on average lei1579.
Other travel options to Chicago, IL take longer:
Bus takes on average 48h 48m.
Train takes on average 49h 18m.
The table below shows live departures for San Diego, CA to Chicago, IL flights for today, Sunday, August 23. You can also manually refresh the results below to see updated flight journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 8:18 PM San Diego, CA | 4h29 | 12:47 AM Chicago, IL | 0 transfersDirect | |
![]() | 11:49 PM San Diego, CA | 4h10 | 3:59 AM Chicago, IL | 0 transfersDirect | |
| Monday, August 24 | |||||
![]() | 12:38 AM San Diego, CA | 4h21 | 4:59 AM Chicago, IL | 0 transfersDirect | |
![]() | 5:35 AM San Diego, CA | 4h04 | 9:39 AM Chicago, IL | 0 transfersDirect | |
![]() | 6:35 AM San Diego, CA | 4h04 | 10:39 AM Chicago, IL | 0 transfersDirect | |
![]() | 3:30 PM San Diego, CA | 8h29 | 11:59 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, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.
Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.
Lively lakefront park with Cloud Gate, Crown Fountain, gardens, and major public art in central Chicago.
Famous shopping boulevard lined with architecture, hotels, riverfront views, and major city energy.
Scenic pedestrian-friendly riverwalk with boat docks, public art, bridges, and standout skyline perspectives.
Deep-dish pizza is Chicago’s iconic pie with a tall buttery crust, layers of cheese and toppings, and chunky tomato sauce baked on top.
The Chicago-style hot dog is an all-beef frank on a poppy seed bun with mustard, relish, onion, tomato, pickle, peppers, and celery salt.
Italian beef is thin-sliced roast beef piled onto a roll, often dipped in savory juices and topped with sweet peppers or spicy giardiniera.
Classic spot for juicy Italian beef sandwiches, especially dipped and topped with spicy giardiniera, with a casual local feel.
Legendary stand for Chicago-style hot dogs and char-grilled sausages, served fast in a no-frills local landmark.
World-famous fine dining destination offering a highly creative tasting menu and refined service in an elegant setting.
Moderate for a major US city: hotels can be pricey, but transit is affordable and dining ranges from cheap eats to upscale options.
Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and optional small change at cafes.
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