$63 Cheap flight deals from San Francisco (SJC) to Oak Brook (CHI)

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This Weekend's Flight Deals from San Francisco to Oak Brook

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Oct 17 - Tue, Oct 20
SFO
San Francisco Intl.
MDW
Midway Intl.
$402 Roundtrip, found 22 hours ago
$402
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Sat, Oct 17 from San Francisco Intl. to Midway Intl., returning Tue, Oct 20, priced at $402 found 22 hours ago
Sat, Oct 17 - Mon, Oct 19
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$418 Roundtrip, found 7 hours ago
$418
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Oct 17 from San Francisco Intl. to O'Hare Intl., returning Mon, Oct 19, priced at $418 found 7 hours ago
Fri, Oct 16 - Tue, Oct 20
OAK
Oakland Intl.
ORD
O'Hare Intl.
$470 Roundtrip, found 7 hours ago
$470
Roundtrip
found 7 hours ago
Select Bargain Flight flight, departing Fri, Oct 16 from Oakland Intl. to O'Hare Intl., returning Tue, Oct 20, priced at $470 found 7 hours ago
Sat, Oct 17 - Tue, Oct 27
OAK
Oakland Intl.
MDW
Midway Intl.
$509 Roundtrip, found 2 days ago
$509
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Oct 17 from Oakland Intl. to Midway Intl., returning Tue, Oct 27, priced at $509 found 2 days ago

Airfares from $63 One Way, $125 Round Trip from San Francisco to Oak Brook

Prices starting at $125 for return flights and $63 for one-way flights to Oak Brook were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Feb 23 - Tue, Mar 2
SFO
San Francisco
ORD
Chicago
$125 Roundtrip, found 3 days ago
$125
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Feb 23 from San Francisco to Chicago, returning Tue, Mar 2, priced at $125 found 3 days ago
Mon, Feb 22 - Fri, Feb 26
SJC
San Jose
ORD
Chicago
$200 Roundtrip, found 5 days ago
$200
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Feb 22 from San Jose to Chicago, returning Fri, Feb 26, priced at $200 found 5 days ago
Thu, Nov 5 - Thu, Nov 12
OAK
Oakland
ORD
Chicago
$205 Roundtrip, found 5 days ago
$205
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Nov 5 from Oakland to Chicago, returning Thu, Nov 12, priced at $205 found 5 days ago
Wed, Nov 11 - Wed, Nov 18
SFO
San Francisco
MDW
Chicago
$212 Roundtrip, found 6 days ago
$212
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Nov 11 from San Francisco to Chicago, returning Wed, Nov 18, priced at $212 found 6 days ago
Wed, Nov 11 - Tue, Nov 17
SFO
San Francisco
MDW
Chicago
$231 Roundtrip, found 6 days ago
$231
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Nov 11 from San Francisco to Chicago, returning Tue, Nov 17, priced at $231 found 6 days ago

Oak Brook economy flight packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

9.2/10 Wonderful! (576 reviews)

Dec 4 - Dec 8

4 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Oakland (OAK)

Frontier Airlines • Coach
Price was $972, price is now $684 per person
$684
per person
found 1 day ago

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.6/10 Exceptional! (2,035 reviews)

Nov 13 - Nov 15

2 night stay

Oakland (OAK) to Chicago (ORD)

Delta • Non-stop • Coach

Chicago (ORD) to Oakland (OAK)

Frontier Airlines • Non-stop • Coach
Price was $1,176, price is now $878 per person
$878
per person
found 1 day ago

The Talbott, Autograph Collection
4.5-star property

The Talbott, Autograph Collection

9.4/10 Exceptional! (179 reviews)

Dec 10 - Dec 13

3 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Price was $894, price is now $687 per person
$687
per person
found 23 hours ago
My biggest issue here is the room I was given, 801. Just not a nice room at all. It's tiny, it had a stale odour, no table/chair, its gloomy, its location, it's a bathtub, not a standalone shower, the mechanics of the door.... If I can say one thing, it is that the bed was comfortable and the fixtures in the bathroom look new. It's just not a place you want to spend any time. The second issue was the length of time to get room service. After many hours of travel, I was too tired to eat out anywhere. I ordered room service and the food was stone cold. The only edible part was the skinny fires that came with the burger. BTW, would be helpful to list the side on the order form as it just said burger... so I ordered separate fries which couldn't be eaten because they were not warm.

Reviewed on Oct 13, 2026

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More About Flying To Oak Brook from San Francisco

Route Information for Flights from San Francisco to Oak Brook

Origin Airport IATA Code
SJC
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

San Francisco to Oak Brook

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.