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San Diego to Chicago Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
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 Sat, Oct 25 - Wed, Oct 29 $264
SAN CHI Sat, Aug 16 - Tue, Aug 26 $308
SAN CHI Wed, Aug 6 - Wed, Aug 13 $322
SAN CHI Sat, Sep 13 - Tue, Sep 16 $344
SAN CHI Tue, Aug 26 - Sat, Aug 30 $344
SAN CHI Tue, Sep 9 - Tue, Sep 16 $356
SAN CHI Wed, Aug 6 - Wed, Aug 13 $358
SAN CHI Sat, Aug 23 - Sat, Sep 6 $402
SAN CHI Wed, Sep 10 - Tue, Sep 16 $544
SAN CHI Tue, Oct 14 - Tue, Oct 21 $678

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, Cathay Pacific, Iberia, US Airways, United Airlines
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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, Cathay Pacific, Iberia, US Airways
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Cheap flights from San Diego to Chicago

Sun Mon Tue Wed Thu Fri Sat
1 2
3 4 5 6 7 8 9
10 11 12 13 14 15 16
17 18 19 20
$276
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 $139

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 165 reviews

O'Hare International Airport Map

Park & Fly - Includes up to 3 nights valet parking

...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 $137

Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
4.1 / 5 68 reviews

6500 SOUTH CICERO AVE Map

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

Hotel only $144

Hilton Garden Inn Chicago/Midway Airport

3 stars
3.6 / 5 22 reviews

6530 S. Cicero Avenue Map

...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 $135

Hampton Inn Chicago-Midway Airport

2 stars
3.8 / 5 30 reviews

6540 S. Cicero Ave. Map

...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 $179

Chicago Marriott Midway

3 stars
3.6 / 5 11 reviews

6520 South Cicero Avenue Map

Rate includes breakfast

...WiFi-equipped guest rooms at our Chicago Midway Airport hotel are recently renovated and offer soundproof windows, 32" flat-screen TVs and room service.... Perfect for business travel and... More

Hotel only $99

Sheraton Chicago O’Hare Airport Hotel

4 stars
4.0 / 5 146 reviews

6501 N. 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

August

Cheapest weekend flights in August from San Diego to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Aug 22 San Diego (SAN) Chicago (MDW) Frontier Airlines $347
Earn $3.47
Return Mon, Aug 25 Chicago (MDW) San Diego (SAN) Frontier Airlines

Lowest roundtrip airfare in August from San Diego to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Aug 20 San Diego (SAN) Chicago (MDW) Frontier Airlines $276
Earn $2.76
Return Wed, Sep 10 Chicago (MDW) San Diego (SAN) Frontier Airlines

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

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Aug 12 San Diego (SAN) Chicago (ORD) Spirit Airlines $308
Earn $3.08
Return Tue, Aug 19 Chicago (ORD) San Diego (SAN) Spirit Airlines
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September

Cheapest weekend flights in September from San Diego to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Sep 11 San Diego (SAN) Chicago (MDW) Frontier Airlines $316
Earn $3.16
Return Sun, Sep 14 Chicago (MDW) San Diego (SAN) Frontier Airlines

Lowest roundtrip airfare in September from San Diego to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Sep 13 San Diego (SAN) Chicago (MDW) Frontier Airlines $264
Earn $2.64
Return Tue, Sep 16 Chicago (MDW) San Diego (SAN) Frontier Airlines

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

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Sep 20 San Diego (SAN) Chicago (ORD) Spirit Airlines $308
Earn $3.08
Return Sat, Sep 27 Chicago (ORD) San Diego (SAN) Spirit Airlines
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October

Cheapest weekend flights in October from San Diego to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 30 San Diego (SAN) Chicago (ORD) Spirit Airlines $328
Earn $3.28
Return Mon, Nov 3 Chicago (ORD) San Diego (SAN) Spirit Airlines

Lowest roundtrip airfare in October from San Diego to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Oct 21 San Diego (SAN) Chicago (MDW) Frontier Airlines $264
Earn $2.64
Return Tue, Oct 28 Chicago (MDW) San Diego (SAN) Frontier Airlines

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

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Oct 21 San Diego (SAN) Chicago (MDW) Frontier Airlines $264
Earn $2.64
Return Tue, Oct 28 Chicago (MDW) San Diego (SAN) Frontier Airlines
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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

    • 19 direct flights are operating from San Diego to Chicago today.
    • Today's average time for a direct flight is 4h 1m.
    • United Airlines flight 532 (1:20 AM GMT, Airbus Industrie A320) is today's earliest available flight from San Diego to Chicago.
    • United Airlines flight 521 (5:40 PM GMT, Airbus Industrie A320) is today's latest available flight from San Diego to Chicago.
    • Today's shortest direct flight from San Diego to Chicago (United Airlines flight 521, Airbus Industrie A320) takes 3h 53m.
    • Today's longest direct flight from San Diego to Chicago (United Airlines flight 532, Airbus Industrie A320) takes 4h 7m.
    • Flights from San Diego Airport (SAN) to Midway Airport (MDW), O'Hare Airport (ORD) are available for this route.

Aircraft options between San Diego and Chicago

Equipment Carrier
Boeing 737-700 Passenger United Airlines, US Airways
Boeing 757-200 Passenger United Airlines, US Airways
Boeing 737-900 Passenger United Airlines, US Airways
Airbus Industrie A319 United Airlines, US Airways
Boeing 737-800 Passenger American Airlines, Alaska Airlines, US Airways, United Airlines, Iberia, Cathay Pacific
Airbus Industrie A320 United Airlines, US Airways