How does KAYAK find such low prices on flights from San Francisco Bay Area to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from San Francisco Bay Area to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Francisco Bay Area to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from San Francisco Bay Area is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from San Francisco Bay Area to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to San Francisco Bay Area with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San Francisco Bay Area to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from San Francisco Bay Area up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$116 CHEAP FLIGHTS from San Francisco Bay Area to Chicago

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Flight Deals

Cheap Flights from San Francisco Bay Area to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from San Francisco Bay Area to Chicago

Wed, Dec 2 - Tue, Dec 8

10:23 pm - 11:46 amOAK Oakland-ORD Chicago O'Hare Intl

11h 23m1 stop Las Vegas Harry Reid Intl

12:51 pm - 9:28 pmORD Chicago O'Hare Intl-OAK Oakland

10h 37m1 stop Las Vegas Harry Reid Intl

$192Frontier

Thu, Oct 22 - Mon, Oct 26

10:17 am - 5:16 amOAK Oakland-ORD Chicago O'Hare Intl

16h 59m1 stop Las Vegas Harry Reid Intl

3:30 pm - 11:53 amORD Chicago O'Hare Intl-OAK Oakland

22h 23m1 stop Las Vegas Harry Reid Intl

$201Frontier

Thu, Nov 5 - Sun, Nov 8

10:18 am - 8:02 pmOAK Oakland-RFD Chicago Greater Rockford

7h 44m1 stop Las Vegas Harry Reid Intl

8:37 pm - 9:23 amRFD Chicago Greater Rockford-OAK Oakland

14h 46m1 stop Las Vegas Harry Reid Intl

$212Multiple Airlines

Tue, Oct 13 - Tue, Oct 20

11:55 pm - 5:55 amOAK Oakland-MDW Chicago Midway

4h 00mnonstop

8:35 pm - 11:20 pmMDW Chicago Midway-OAK Oakland

4h 45mnonstop

$231Southwest

Thu, Nov 5 - Sun, Nov 8

10:18 am - 8:02 pmOAK Oakland-RFD Chicago Greater Rockford

7h 44m1 stop Las Vegas Harry Reid Intl

8:37 pm - 9:23 amRFD Chicago Greater Rockford-OAK Oakland

14h 46m1 stop Las Vegas Harry Reid Intl

$233Multiple Airlines

Tue, Oct 13 - Tue, Oct 20

11:55 pm - 5:55 amOAK Oakland-MDW Chicago Midway

4h 00mnonstop

5:50 pm - 10:10 pmMDW Chicago Midway-OAK Oakland

6h 20m1 stop Las Vegas Harry Reid Intl

$241Southwest

Tue, Dec 15 - Tue, Jan 5

1:36 pm - 11:59 pmOAK Oakland-ORD Chicago O'Hare Intl

8h 23m1 stop Seattle/Tacoma Intl

2:11 pm - 7:25 pmORD Chicago O'Hare Intl-OAK Oakland

7h 14m1 stop Portland

$251Alaska Airlines

Tue, Oct 27 - Wed, Oct 28

7:04 am - 6:53 pmOAK Oakland-ORD Chicago O'Hare Intl

9h 49m1 stop San Diego

3:49 pm - 10:55 pmORD Chicago O'Hare Intl-OAK Oakland

9h 06m1 stop Seattle/Tacoma Intl

$251Alaska Airlines

Wed, Oct 21 - Tue, Oct 27

12:41 pm - 10:05 pmOAK Oakland-ORD Chicago O'Hare Intl

7h 24m1 stop Salt Lake City

1:55 pm - 11:56 pmORD Chicago O'Hare Intl-OAK Oakland

12h 01m2 stops Detroit Metropolitan Wayne County Salt Lake City

$256Delta

Wed, Dec 2 - Tue, Dec 8

5:07 pm - 8:46 amOAK Oakland-ORD Chicago O'Hare Intl

13h 39m2 stops Salt Lake City Atlanta Hartsfield-Jackson

7:25 am - 11:54 amORD Chicago O'Hare Intl-OAK Oakland

6h 29m1 stop Salt Lake City

$256Delta

Recent last minute flight deals from San Francisco Bay Area to Chicago

Tue, Sep 22 - Tue, Oct 20

7:11 pm - 5:38 amSFO San Francisco-ORD Chicago O'Hare Intl

8h 27m1 stop Las Vegas Harry Reid Intl

8:01 pm - 8:38 pmORD Chicago O'Hare Intl-SFO San Francisco

26h 37m1 stop Los Angeles

$258Frontier

Tue, Sep 22 - Wed, Oct 21

7:11 pm - 5:38 amSFO San Francisco-ORD Chicago O'Hare Intl

8h 27m1 stop Las Vegas Harry Reid Intl

6:30 am - 11:05 amORD Chicago O'Hare Intl-SFO San Francisco

6h 35m1 stop Denver Intl

$266Frontier

Tue, Sep 22 - Sat, Oct 17

7:11 pm - 5:38 amSFO San Francisco-ORD Chicago O'Hare Intl

8h 27m1 stop Las Vegas Harry Reid Intl

7:20 am - 12:41 pmORD Chicago O'Hare Intl-SFO San Francisco

7h 21m1 stop San Diego

$283Multiple Airlines

Thu, Sep 17 - Sun, Sep 20

10:17 am - 8:39 pmOAK Oakland-RFD Chicago Greater Rockford

8h 22m1 stop Las Vegas Harry Reid Intl

9:29 pm - 9:22 amRFD Chicago Greater Rockford-OAK Oakland

13h 53m1 stop Las Vegas Harry Reid Intl

$330Multiple Airlines

Wed, Sep 23 - Tue, Oct 20

11:40 pm - 5:50 amSFO San Francisco-MDW Chicago Midway

4h 10mnonstop

8:55 pm - 11:40 pmMDW Chicago Midway-SFO San Francisco

4h 45mnonstop

$382Southwest

Wed, Sep 23 - Tue, Oct 20

11:40 pm - 5:50 amSFO San Francisco-MDW Chicago Midway

4h 10mnonstop

6:05 am - 11:25 amMDW Chicago Midway-SFO San Francisco

7h 20m1 stop Las Vegas Harry Reid Intl

$392Southwest

Tue, Sep 22 - Fri, Oct 23

7:22 pm - 6:20 amSFO San Francisco-ORD Chicago O'Hare Intl

8h 58m1 stop Seattle/Tacoma Intl

7:20 am - 12:41 pmORD Chicago O'Hare Intl-SFO San Francisco

7h 21m1 stop San Diego

$392Alaska Airlines

Tue, Sep 22 - Mon, Oct 19

10:46 pm - 5:00 amSFO San Francisco-ORD Chicago O'Hare Intl

4h 14mnonstop

6:45 am - 9:37 amORD Chicago O'Hare Intl-SFO San Francisco

4h 52mnonstop

$398American Airlines

Tue, Sep 22 - Mon, Oct 19

9:29 am - 8:00 pmSFO San Francisco-ORD Chicago O'Hare Intl

8h 31m1 stop Los Angeles

6:45 am - 9:37 amORD Chicago O'Hare Intl-SFO San Francisco

4h 52mnonstop

$408American Airlines

Mon, Sep 21 - Fri, Oct 23

10:32 am - 7:21 pmSFO San Francisco-ORD Chicago O'Hare Intl

6h 49m1 stop San Diego

5:46 pm - 11:52 pmORD Chicago O'Hare Intl-SFO San Francisco

8h 06m1 stop Seattle/Tacoma Intl

$426Alaska Airlines

Recent direct flight deals from San Francisco Bay Area to Chicago

Tue, Oct 13 - Tue, Oct 20

11:55 pm - 5:55 amOAK Oakland-MDW Chicago Midway

4h 00mnonstop

8:35 pm - 11:20 pmMDW Chicago Midway-OAK Oakland

4h 45mnonstop

$231Southwest

Thu, Oct 22 - Mon, Oct 26

3:18 pm - 9:50 pmSFO San Francisco-ORD Chicago O'Hare Intl

4h 32mnonstop

6:45 am - 9:37 amORD Chicago O'Hare Intl-SFO San Francisco

4h 52mnonstop

$263American Airlines

Mon, Oct 19 - Thu, Oct 22

5:00 am - 11:25 amSFO San Francisco-ORD Chicago O'Hare Intl

4h 25mnonstop

4:05 pm - 6:54 pmORD Chicago O'Hare Intl-SFO San Francisco

4h 49mnonstop

$263United Airlines

Sun, Oct 18 - Thu, Oct 22

12:35 am - 6:56 amSFO San Francisco-ORD Chicago O'Hare Intl

4h 21mnonstop

4:05 pm - 6:54 pmORD Chicago O'Hare Intl-SFO San Francisco

4h 49mnonstop

$263United Airlines

Mon, Oct 12 - Thu, Oct 15

6:00 am - 12:34 pmSFO San Francisco-ORD Chicago O'Hare Intl

4h 34mnonstop

9:31 pm - 12:30 amORD Chicago O'Hare Intl-SFO San Francisco

4h 59mnonstop

$263American Airlines

Thu, Feb 11 - Mon, Feb 15

10:35 am - 4:35 pmSFO San Francisco-MDW Chicago Midway

4h 00mnonstop

10:10 am - 12:50 pmMDW Chicago Midway-SFO San Francisco

4h 40mnonstop

$263Southwest

Mon, Oct 19 - Thu, Oct 22

11:40 pm - 5:50 amSFO San Francisco-MDW Chicago Midway

4h 10mnonstop

9:25 pm - 12:10 amMDW Chicago Midway-SFO San Francisco

4h 45mnonstop

$263Southwest

Thu, Oct 22 - Mon, Oct 26

3:18 pm - 9:50 pmSFO San Francisco-ORD Chicago O'Hare Intl

4h 32mnonstop

9:31 pm - 12:30 amORD Chicago O'Hare Intl-SFO San Francisco

4h 59mnonstop

$263American Airlines

Mon, Jan 11 - Mon, Jan 18

6:05 am - 12:05 pmSFO San Francisco-MDW Chicago Midway

4h 00mnonstop

9:15 pm - 11:55 pmMDW Chicago Midway-SFO San Francisco

4h 40mnonstop

$263Southwest

Wed, Nov 11 - Wed, Dec 9

6:30 am - 12:54 pmSJC San Jose-ORD Chicago O'Hare Intl

4h 24mnonstop

9:07 am - 11:59 amORD Chicago O'Hare Intl-SJC San Jose

4h 52mnonstop

$401United Airlines

Useful Info

Low season	January
High season	June
Cheapest flight	$116

Best time to beat the crowds with an average 5% drop in price.

Most popular time to fly with an average 4% increase in price.

Flight from Oakland to Chicago Midway Airport

How does KAYAK find such low prices on flights from San Francisco Bay Area to Chicago?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from San Francisco Bay Area to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Francisco Bay Area to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from San Francisco Bay Area is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from San Francisco Bay Area to Chicago?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to San Francisco Bay Area with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San Francisco Bay Area to Chicago?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from San Francisco Bay Area up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.