join Orbitz Rewards

By clicking, I agree to the terms

San Diego to Chicago Flights

Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Selected fares from San Diego to Chicago

Departure Arrival Travel dates Round-trip
SAN CHI Fri, Apr 17 - Tue, Apr 21 $197
SAN CHI Tue, Mar 3 - Tue, Mar 10 $290
SAN CHI Wed, Mar 11 - Wed, Mar 18 $302
SAN CHI Thu, Feb 26 - Tue, Mar 3 $320
SAN CHI Thu, Feb 26 - Tue, Mar 3 $320
SAN CHI Thu, Mar 12 - Mon, Mar 16 $375
SAN CHI Tue, May 26 - Thu, May 28 $400
SAN CHI Fri, May 1 - Sun, May 3 $400
SAN CHI Thu, Mar 12 - Mon, Mar 16 $413
SAN CHI Tue, Feb 24 - Tue, Mar 10 $490

San Diego and Chicago airports and terminals

Airports in San Diego CA, US
map of airports in San Diego
  • 1

    San Diego Airport (SAN)

    Distance from City Center: 2 miles

    Terminals and carriers for flights from SAN to CHI

    Terminal Carriers
    Terminal 1 US Airways, United Airlines
    Terminal 2 Alaska Airlines, American Airlines, British Airways, Cathay Pacific, Iberia, US Airways, United Airlines
Back to menu Return to top

Airports in Chicago IL, US
map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

    Terminals and carriers for flights from SAN to ORD

    Terminal Carriers
    Terminal 1 US Airways, United Airlines
    Terminal 3 Alaska Airlines, American Airlines, British Airways, Cathay Pacific, Iberia, US Airways
Back to menu Return to top
Sun Mon Tue Wed Thu Fri Sat
1 2 3
$285
4
$285
5 6 7
8 9 10 11 12 13 14
15 16 17
$285
18 19 20 21
22 23 24 25 26 27 28
29 30 31

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Chicago Airport Hotels

Hotel only $79

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 128 reviews

O'Hare International Airport Map

Rate Includes Breakfast

...This O'Hare airport hotel is located in Terminal 2 and is within walking distance to all O'Hare Airport's domestic terminals.... More

Hotel only $120

Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
4.1 / 5 43 reviews

6500 South Cicero Avenue Map

Exceptional Hotel Near Chicago Midway Airport Searching for hotels near the best sights in downtown Chicago?... More

Hotel only $118

Hilton Garden Inn Chicago/Midway Airport

3 stars
3.7 / 5 15 reviews

6530 S. Cicero Avenue Map

Complimentary wired and Wi-Fi Internet Access

...Advance Purchase Rate online!The Hilton Garden Inn Chicago Midway Airport in Chicago is located on the Midway Hotel Center campus just two blocks south of the Chicago Midway Airport and the... More

Hotel only $118

Hampton Inn Chicago-Midway Airport

2 stars
3.8 / 5 17 reviews

6540 S. Cicero Ave. Map

Free On The HouseT hot breakfast, Wi-Fi

...And no matter what time your flight got in or is going out, we're here to pick you up or drop you off.... land here and let your vacation take off...welcome to the Hampton Inn Chicago-Midway... More

Hotel only $159

Chicago Marriott Midway

3 stars
3.7 / 5 7 reviews

6520 South Cicero Avenue Map

Rate includes breakfast

Perfect for business travel and weekend getaways, the renovated Marriott Chicago Midway is just two blocks from MDW airport and offers a free 24-hr shuttle.... More

Hotel only $87

Sheraton Chicago O'Hare Airport Hotel

4 stars
4.0 / 5 115 reviews

6501 North Mannheim Road Map

Save 15% on your stay, Breakfast Included

...Complimentary shuttle service to and from O'Hare Airport is available 24 hours a day.... Our all-suite hotel is conveniently located minutes from O'Hare International Airport, Donald E. Stephens... More

March

Cheapest weekend flights in March from San Diego to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Mar 7 San Diego (SAN) Chicago (ORD) Frontier Airlines $294
Earn $2.94
Return Mon, Mar 9 Chicago (ORD) San Diego (SAN) Frontier Airlines

Lowest roundtrip airfare in March from San Diego to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Mar 17 San Diego (SAN) Chicago (ORD) Spirit Airlines $285
Earn $2.85
Return Tue, Mar 24 Chicago (ORD) San Diego (SAN) Spirit Airlines

Best one-week trip in March from San Diego to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Mar 17 San Diego (SAN) Chicago (ORD) Spirit Airlines $285
Earn $2.85
Return Tue, Mar 24 Chicago (ORD) San Diego (SAN) Spirit Airlines
Back to menu Return to top

April

Cheapest weekend flights in April from San Diego to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Apr 17 San Diego (SAN) Chicago (ORD) Spirit Airlines $197
Earn $1.97
Return Mon, Apr 20 Chicago (ORD) San Diego (SAN) Spirit Airlines

Lowest roundtrip airfare in April from San Diego to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Apr 29 San Diego (SAN) Chicago (ORD) Spirit Airlines $197
Earn $1.97
Return Tue, May 5 Chicago (ORD) San Diego (SAN) Spirit Airlines

Best one-week trip in April from San Diego to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Apr 18 San Diego (SAN) Chicago (ORD) Spirit Airlines $227
Earn $2.27
Return Sat, Apr 25 Chicago (ORD) San Diego (SAN) Spirit Airlines
Back to menu Return to top

May

Cheapest weekend flights in May from San Diego to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, May 8 San Diego (SAN) Chicago (ORD) Spirit Airlines $257
Earn $2.57
Return Mon, May 11 Chicago (ORD) San Diego (SAN) Spirit Airlines

Lowest roundtrip airfare in May from San Diego to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, May 12 San Diego (SAN) Chicago (ORD) Spirit Airlines $197
Earn $1.97
Return Wed, May 20 Chicago (ORD) San Diego (SAN) Spirit Airlines

Best one-week trip in May from San Diego to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, May 5 San Diego (SAN) Chicago (ORD) Spirit Airlines $197
Earn $1.97
Return Tue, May 12 Chicago (ORD) San Diego (SAN) Spirit Airlines
Back to menu Return to top

Finding Flights from San Diego to Chicago

San Diego's Airport

Orbitz.com can help you find cheap flights from San Diego for your next trip. San Diego International Airport, also known as Lindbergh Field, is located on San Diego Bay, three miles from downtown. The airport is the busiest single-runway airport in the United States. Domestic and international flights are provided by 20 different airlines, including JetBlue, Delta, Southwest, United and US Airways.

Airport Parking Information

The San Diego International Airport offers both hourly and long-term parking spaces. Short-term parking is offered at $4 per hour and long-term parking costs between $11 and $28 per day. You can park your car for up to 30 days. Be aware that curbside parking is never permitted at San Diego International Airport.

Ground Transportation Information

If you would prefer not to leave your car at the airport, metered taxis are available to transport you to the airport. Taxi fares are approximately $2.20 for the first 1/10 mile and $2.30 for each additional mile. San Diego also has a bus system, with a fare of $2.50-$5.00. Not only can Orbitz.com help you plan your discount air travel, it can also help you plan your ground transportation.

San Diego Airport Restaurants

There are many restaurant options available at the San Diego International Airport. You can grab a bite to eat at Chili's To Go, Starbucks, McDonald's or many other restaurants while waiting for your flight. There is also an NFL Bar. There is a variety of shops where you can purchase anything from books to cell phones. Keep checking Orbitz.com for cheap flights from San Diego.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Interesting facts about flights from San Diego to Chicago

    • 8 direct flights are operating from San Diego to Chicago today.
    • Today's average time for a direct flight is 4h 2m.
    • United Airlines flight 1608 (2:47 AM GMT, Boeing 737-700 Passenger) is today's earliest available flight from San Diego to Chicago.
    • American Airlines flight 936 (6:10 AM GMT, Boeing 737-800 Passenger) is today's latest available flight from San Diego to Chicago.
    • Today's shortest direct flight from San Diego to Chicago (American Airlines flight 936, Boeing 737-800 Passenger) takes 3h 59m.
    • Today's longest direct flight from San Diego to Chicago (United Airlines flight 1608, Boeing 737-700 Passenger) takes 4h 7m.
    • Flights from San Diego Airport (SAN) to Midway Airport (MDW), O'Hare Airport (ORD) are available for this route.

Flight schedule for flights from San Diego to Chicago on Mon, Feb 2, 2015

Carrier Flight # Departing Arriving Aircraft Flight time
Airport Time Airport Time
American Airlines/US Airways AA486/US486 SAN 4:15 PM ORD 12:02 AM 321/321 5hr 47min
American Airlines AA486 SAN 4:15 PM ORD 12:02 AM 321 5hr 47min
US Airways US486 SAN 4:15 PM ORD 12:02 AM 321 5hr 47min
US Airways/American Airlines US486/AA486 SAN 4:15 PM ORD 12:02 AM 321/321 5hr 47min
American Airlines/United Airlines AA2590/UA660 SAN 8:10 PM ORD 5:24 AM CRJ/320 7hr 14min
US Airways/United Airlines US2590/UA660 SAN 8:10 PM ORD 5:24 AM CRJ/320 7hr 14min
American Airlines/US Airways AA2590/US1062 SAN 8:10 PM ORD 5:50 AM CRJ/738 7hr 40min
American Airlines/American Airlines AA2590/AA1062 SAN 8:10 PM ORD 5:50 AM CRJ/738 7hr 40min
US Airways/US Airways US2590/US1062 SAN 8:10 PM ORD 5:50 AM CRJ/738 7hr 40min
US Airways/American Airlines US2590/AA1062 SAN 8:10 PM ORD 5:50 AM CRJ/738 7hr 40min
Alaska Airlines/American Airlines AS5563/AA3148 SAN 10:30 PM ORD 7:15 AM 320/ER4 6hr 45min
Alaska Airlines/Alaska Airlines AS5563/AS4174 SAN 10:30 PM ORD 7:15 AM 320/ER4 6hr 45min
Alaska Airlines/US Airways AS5563/US8381 SAN 10:30 PM ORD 7:15 AM 320/ER4 6hr 45min