Flights from San Diego to Chicago

Selected fares from San Diego to Chicago

Departure
Arrival
Travel dates
Round-trip

Departure:

SAN

Arrival:

CHI

Travel dates

Thu, Aug 27 - Wed, Sep 2

Round-trip

Departure:

SAN

Arrival:

CHI

Travel dates

Sun, Aug 9 - Thu, Aug 20

Round-trip

Departure:

SAN

Arrival:

CHI

Travel dates

Mon, Aug 31 - Tue, Sep 1

Round-trip

Departure:

SAN

Arrival:

CHI

Travel dates

Wed, Nov 11 - Sat, Nov 14

Round-trip

Departure:

SAN

Arrival:

CHI

Travel dates

Wed, Sep 9 - Fri, Sep 11

Round-trip

Departure:

SAN

Arrival:

CHI

Travel dates

Fri, Nov 6 - Mon, Nov 9

Round-trip

Departure:

SAN

Arrival:

CHI

Travel dates

Wed, Aug 26 - Sun, Aug 30

Round-trip

Departure:

SAN

Arrival:

CHI

Travel dates

Wed, Aug 19 - Sat, Aug 22

Round-trip

Departure:

SAN

Arrival:

CHI

Travel dates

Wed, Aug 19 - Sat, Aug 22

Round-trip

Departure:

SAN

Arrival:

CHI

Travel dates

Wed, Nov 4 - Wed, Nov 11

Round-trip

September 2015
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Leaving Sat, Sep 12

13
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Leaving Wed, Sep 16

17
Thu, Sep 17
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= Cheapest round-trip flights

* Prices are round trip per person (conditions apply)

Save more with Chicago Flight + Hotel packages

San Diego and Chicago airports and terminals

Airports in San Diego CA, US

San Diego

Airports in Chicago IL, US

Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

    Carriers

  • 2

    O'Hare International Airport (ORD)

    Distance from City Center: 15.1 miles

    Terminals and carriers for flights from SAN to ORD

    Terminal

    Carriers

    Terminal 1
    United Airlines
    Terminal 3
    Alaska Airlines, American Airlines, Spirit Airlines, US Airways

  

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Featured Chicago Airport Hotels

http://www.tnetnoc.com/hotelphotos/890/40890/2631759-Hilton-Chicago-OHare-Airport-Hotel-Exterior-1-LP.jpg
O'Hare International Airport Map
3.9 / 5 162 reviews
  • Rate Includes Breakfast
  • Rate Includes Breakfast
From
$99

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

From
$99
http://www.tnetnoc.com/hotelphotos/298/23298/2631759-Holiday-Inn-Express-Suites-CHICAGO-MIDWAY-AIRPORT-Hotel-Exterior-1-LP.jpg
6500 South Cicero Avenue Map
4.2 / 5 56 reviews
From
$146

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

From
$146
http://www.tnetnoc.com/hotelphotos/815/85815/2631759-Hilton-Garden-Inn-ChicagoMidway-Airport-Hotel-Exterior-1-LP.jpg
6530 S. Cicero Avenue Map
3.6 / 5 17 reviews
  • Complimentary wired and Wi-Fi Internet Access
  • Complimentary wired and Wi-Fi Internet Access
From
$152

...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

From
$152
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6550 S. Cicero Avenue Map
Not yet reviewed
From
$143

...Located just 1 mile south of Chicago International Airport, Hyatt offers a complementary 24 hour shuttle to and from the airport.... Midway Hotel Centers newest property is composed of 6 floors,... More

From
$143
http://www.tnetnoc.com/hotelphotos/232/29232/2631759-Hampton-Inn-Chicago-Midway-Airport-Hotel-Exterior-2-LP.jpg
6540 S. Cicero Ave. Map
3.8 / 5 17 reviews
  • Free On The House hot breakfast, Wi-Fi
  • Free On The House hot breakfast, Wi-Fi
From
$135

...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

From
$135

September

Cheapest weekend flights in September from San Diego to Chicago

Leave
Sat, Sep 26
San Diego
(SAN)
Chicago
(ORD)
Spirit Airlines
Spirit Airlines
Return
Mon, Sep 28
Chicago
(ORD)
San Diego
(SAN)
Spirit Airlines
Spirit Airlines
Earn $1.87

Lowest roundtrip airfare in September from San Diego to Chicago

Leave
Tue, Sep 22
San Diego
(SAN)
Chicago
(ORD)
Spirit Airlines
Spirit Airlines
Return
Tue, Oct 13
Chicago
(ORD)
San Diego
(SAN)
Spirit Airlines
Spirit Airlines
Earn $1.77

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

Leave
Wed, Sep 9
San Diego
(SAN)
Chicago
(ORD)
Spirit Airlines
Spirit Airlines
Return
Wed, Sep 16
Chicago
(ORD)
San Diego
(SAN)
Spirit Airlines
Spirit Airlines
Earn $1.99

October

Cheapest weekend flights in October from San Diego to Chicago

Leave
Thu, Oct 22
San Diego
(SAN)
Chicago
(ORD)
Spirit Airlines
Spirit Airlines
Return
Mon, Oct 26
Chicago
(ORD)
San Diego
(SAN)
Spirit Airlines
Spirit Airlines
Earn $1.97

Lowest roundtrip airfare in October from San Diego to Chicago

Leave
Sat, Oct 24
San Diego
(SAN)
Chicago
(ORD)
Spirit Airlines
Spirit Airlines
Return
Tue, Oct 27
Chicago
(ORD)
San Diego
(SAN)
Spirit Airlines
Spirit Airlines
Earn $1.77

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

Leave
Tue, Oct 6
San Diego
(SAN)
Chicago
(ORD)
Spirit Airlines
Spirit Airlines
Return
Tue, Oct 13
Chicago
(ORD)
San Diego
(SAN)
Spirit Airlines
Spirit Airlines
Earn $1.77

November

Cheapest weekend flights in November from San Diego to Chicago

Leave
Thu, Nov 5
San Diego
(SAN)
Chicago
(ORD)
Spirit Airlines
Spirit Airlines
Return
Sun, Nov 8
Chicago
(ORD)
San Diego
(SAN)
Spirit Airlines
Spirit Airlines