Cheap flights from Oakland (SJC) to Chicago (CHI)

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Lowest round trip fares by airline from Oakland and Chicago

Cheapest prices ($69 One Way, $128 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, May 29 - Fri, Jun 7
SFO
San Francisco
MDW
Chicago
$128 Roundtrip, found 1 day ago
$128
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, May 29 from San Francisco to Chicago, returning Fri, Jun 7, priced at $128 found 1 day ago
Wed, May 29 - Wed, Jun 5
SFO
San Francisco
MDW
Chicago
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, May 29 from San Francisco to Chicago, returning Wed, Jun 5, priced at $155 found 1 day ago
Wed, May 29 - Fri, May 31
OAK
Oakland
ORD
Chicago
$161 Roundtrip, found 2 hours ago
$161
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Wed, May 29 from Oakland to Chicago, returning Fri, May 31, priced at $161 found 2 hours ago
Wed, May 29 - Tue, Jun 11
SJC
San Jose
ORD
Chicago
$164 Roundtrip, found 8 hours ago
$164
Roundtrip
found 8 hours ago
Select Spirit Airlines flight, departing Wed, May 29 from San Jose to Chicago, returning Tue, Jun 11, priced at $164 found 8 hours ago
Sat, Aug 17 - Sat, Aug 24
SFO
San Francisco
ORD
Chicago
$174 Roundtrip, found 5 days ago
$174
Roundtrip
found 5 days ago
Select Bargain Flight flight, departing Sat, Aug 17 from San Francisco to Chicago, returning Sat, Aug 24, priced at $174 found 5 days 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! (1,009 reviews)
"I love this place! I’ve stayed here 3 times and it’s always good service and polite staff. The area is perfect. I highly recommend it."

Reviewed on May 9, 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 $112 per night from May 27 to May 28
$112
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 (1,642 reviews)
"I loved the location close to other attractions."

Reviewed on May 10, 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 26 to May 27
$60
per night
May 26 - May 27
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 Oakland to Chicago

Origin
Oakland
Destination
Chicago
Number of Daily Flights
76
Earliest Flight Departure Date
May 20
Latest Flight Departure Date
May 21
Popular Airlines
United Airlines

Cheap flights from Oakland to Chicago

Oakland Metropolitan Oak International (OAK) is a modestly sized international airport offering frequent flights to Chicago Ohare International (ORD). Public transit offers simple and easy access to OAK, with BART running from downtown Oakland, San Francisco and Berkeley directly to the airport. Flights to ORD average 7 to 9 hours.

Upon arrival, grab a cab by heading to the lower-level curb front area next to the baggage claim. Free shuttles to all rental car companies are located outside baggage claim as well. Regional buses also offer rides to further destinations outside of the greater Chicago area.

Attractions and Tips

The Art Institute of Chicago is an internationally celebrated must for art lovers. The Briar Street Theatre, home of the popular performers of the Blue Man Group, is just a half hour drive from ORD and offers exciting live entertainment.

Baseball fans can see the Cubs at the legendary Wrigley Field during baseball season.

Chicago’s weather varies from frigid extremes in the winter months (often accompanied by snow and rain), and warm, but not blistering, in the summer. Visitors who travel during winter should check the status of flights that may be hindered due to snow, rain or ice.

When choosing a hotel, explore the whole city, as many neighborhoods highlight boutique and large chain establishments alike.

Flights from Cities near Oakland

Flights to Cities near Chicago

Other Flights to Chicago

Other Flights from Oakland

*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.