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Lowest round trip fares by airline from San Francisco and Chicago

Cheapest prices ($69 One Way, $108 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Sep 25 - Sat, Sep 28
SFO
San Francisco
MDW
Chicago
$108 Roundtrip, found 3 hours ago
$108
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Sep 25 from San Francisco to Chicago, returning Sat, Sep 28, priced at $108 found 3 hours ago
Wed, May 29 - Fri, May 31
OAK
Oakland
ORD
Chicago
$161 Roundtrip, found 1 day ago
$161
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, May 29 from Oakland to Chicago, returning Fri, May 31, priced at $161 found 1 day ago
Wed, May 29 - Tue, Jun 11
SJC
San Jose
ORD
Chicago
$164 Roundtrip, found 2 days ago
$164
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, May 29 from San Jose to Chicago, returning Tue, Jun 11, priced at $164 found 2 days ago
Wed, Aug 14 - Sat, Aug 17
SFO
San Francisco
ORD
Chicago
$174 Roundtrip, found 1 day ago
$174
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Aug 14 from San Francisco to Chicago, returning Sat, Aug 17, priced at $174 found 1 day ago
Tue, Aug 13 - Wed, Aug 14
SFO
San Francisco
ORD
Chicago
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Select United flight, departing Tue, Aug 13 from San Francisco to Chicago, returning Wed, Aug 14, priced at $179 found 1 day ago

Great Deals On Cheap Hotels in Chicago

Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
The price is $94 per night from May 27 to May 28
$94
per night
May 27 - May 28
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.6/10 Good! (1,004 reviews)
"I’ve stayed many times and enjoyed the Freehand."

Reviewed on May 13, 2024

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
The price is $93 per night from May 27 to May 28
$93
per night
May 27 - May 28
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
6.4/10 (1,644 reviews)
"Could use some updates on the mattresses"

Reviewed on May 14, 2024

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
The price is $60 per night from May 28 to May 29
$60
per night
May 28 - May 29
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
8/10 Very Good! (1,173 reviews)
"The website said breakfast and pool included but they only have coffee fyi though there’s some food places nearby and i couldn’t find a pool. One of the better Motel 6s I’ve stayed at though and the staff let us in our room early which was really convenient"

Reviewed on May 12, 2024

Motel 6 Elk Grove Village, IL - O'Hare
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From San Francisco to Chicago

Origin
San Francisco
Destination
Chicago
Number of Daily Flights
78
Earliest Flight Departure Date
May 22
Latest Flight Departure Date
May 23
Popular Airlines
United Airlines

Cheap flights from San Francisco to Chicago

If you fly from San Francisco to Chicago, you will find quite a contrast between the hilly city of San Francisco and the flat city of Chicago. Dependable transportation will make it easy for you to visit all of Chicago's nearby attractions.

It is best to rent a car at Chicago O'Hare International Airport (ORD), then you can head over to Lake Park to get some fresh air. You can relax in the gazebo or stroll along the path next to Lake Opeka. When you have spent enough time enjoying nature, take your car into the city to see the sights.

Key Facts

If you want to spend some time near the airport, before heading into the city, you can visit Frank Lloyd Wright's studio and home in Oak Park. There you will be able to see Wright's drafting room in the studio. The Kohl Children's Museum in Glenview can easily be reached by car. The museum features interactive exhibits, such as an art exhibit where children can paint and play with clay.

Hints and Tips

The flight from San Francisco International Airport (SFO) to Chicago takes approximately four and a half hours. Visit the Chicago History Museum to learn about the city's transformation from a frontier town, into a bustling metropolis.

Flights from Cities near San Francisco

Flights to Cities near Chicago

Other Flights to Chicago

Other Flights from San Francisco

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.