$79 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.
SFO
San Francisco Intl.
MDW
Midway Intl.
$338 Roundtrip, just found
$338
Roundtrip
just found
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$369 Roundtrip, just found
$369
Roundtrip
just found
OAK
Oakland Intl.
ORD
O'Hare Intl.
$378 Roundtrip, found 1 day ago
$378
Roundtrip
found 1 day ago
OAK
Oakland Intl.
MDW
Midway Intl.
$489 Roundtrip, found 1 day ago
$489
Roundtrip
found 1 day ago
Airfares from $79 One Way, $158 Round Trip from San Francisco to Oak Brook
Prices starting at $158 for return flights and $79 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.
SFO
San Francisco
MDW
Chicago
$158 Roundtrip, found 2 hours ago
$158
Roundtrip
found 2 hours ago
SJC
San Jose
ORD
Chicago
$158 Roundtrip, found 6 hours ago
$158
Roundtrip
found 6 hours ago
OAK
Oakland
ORD
Chicago
$158 Roundtrip, found 9 hours ago
$158
Roundtrip
found 9 hours ago
SFO
San Francisco
ORD
Chicago
$158 Roundtrip, found 1 hour ago
$158
Roundtrip
found 1 hour ago
SFO
San Francisco
RFD
Rockford
$219 Roundtrip, found 3 days ago
$219
Roundtrip
found 3 days ago
Oak Brook economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Swissotel - Chicago
9/10 Wonderful! (3,537 reviews)
Sep 18 - Sep 21
3 night stay
Oakland (OAK) to Chicago (ORD)
Southwest Airlines • Roundtrip • Coach
Price was $1,334, price is now $966 per person
$966
per person
found 1 day ago
Always a great stay at The Swiss. Got upgraded to a corner room at no charge. Great views of the lake and the river. Paloma’s at the bar were great. Breakfast was awesome as well. Had the croissant sandwich and Belgian waffle.
Reviewed on Aug 17, 2026
4.0-star property
Level Chicago - River North
9.2/10 Wonderful! (1,043 reviews)
Sep 17 - Sep 20
3 night stay
San Francisco (SFO) to Chicago (ORD)
Alaska Airlines • Non-stop • Coach
Chicago (ORD) to San Francisco (SFO)
Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,501, price is now $1,055 per person
$1,055
per person
found 1 day ago
5.0-star property
The Peninsula Chicago
9.8/10 Exceptional! (1,003 reviews)
Sep 17 - Sep 20
3 night stay
San Francisco (SFO) to Chicago (ORD)
Alaska Airlines • Non-stop • Coach
Chicago (ORD) to San Francisco (SFO)
Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,061, price is now $1,519 per person
$1,519
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from San Francisco to Oak Brook
View all tripsOak Brook packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Swissotel - Chicago
9/10 Wonderful! (3,537 reviews)
Oct 3 - Oct 6
3 night stay
San Francisco (SFO) to Chicago (ORD)
Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,131, price is now $767 per person
$767
per person
found 1 day ago
Always a great stay at The Swiss. Got upgraded to a corner room at no charge. Great views of the lake and the river. Paloma’s at the bar were great. Breakfast was awesome as well. Had the croissant sandwich and Belgian waffle.
Reviewed on Aug 17, 2026
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (4,907 reviews)
Oct 3 - Oct 6
3 night stay
San Francisco (SFO) to Chicago (ORD)
Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,333, price is now $857 per person
$857
per person
found 1 day ago
I had an amazing time at the hotel. The employees were helpful and the rooftop view is amazing.
Reviewed on Aug 17, 2026
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
9.4/10 Exceptional! (2,638 reviews)
Oct 3 - Oct 6
3 night stay
San Francisco (SFO) to Chicago (ORD)
Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,295, price is now $873 per person
$873
per person
found 1 day ago
It was a good stay. Views, room cleaning everyday and convenient, but you will spend a lot going back and forth to the magnificent mile. No pool but has a Ferris wheel . I recommend.
Reviewed on Aug 17, 2026
Don't see what you're looking for?
See all available trips from San Francisco to Oak Brook
View all tripsOak Brook first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Swissotel - Chicago
9/10 Wonderful! (3,537 reviews)
Oct 7 - Oct 10
3 night stay
San Francisco (SFO) to Chicago (ORD)
United • FirstClass
Chicago (ORD) to San Francisco (SFO)
Alaska Airlines • FirstClass
Price was $2,089, price is now $1,708 per person
$1,708
per person
found 1 day ago
Always a great stay at The Swiss. Got upgraded to a corner room at no charge. Great views of the lake and the river. Paloma’s at the bar were great. Breakfast was awesome as well. Had the croissant sandwich and Belgian waffle.
Reviewed on Aug 17, 2026
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
9.4/10 Exceptional! (2,638 reviews)
Oct 7 - Oct 10
3 night stay
San Francisco (SFO) to Chicago (ORD)
United • FirstClass
Chicago (ORD) to San Francisco (SFO)
Alaska Airlines • FirstClass
Price was $2,397, price is now $1,953 per person
$1,953
per person
found 1 day ago
It was a good stay. Views, room cleaning everyday and convenient, but you will spend a lot going back and forth to the magnificent mile. No pool but has a Ferris wheel . I recommend.
Reviewed on Aug 17, 2026
4.5-star property
Fairmont Chicago at Millennium Park
8.8/10 Excellent! (2,293 reviews)
Oct 7 - Oct 10
3 night stay
San Francisco (SFO) to Chicago (ORD)
United • FirstClass
Chicago (ORD) to San Francisco (SFO)
Alaska Airlines • FirstClass
Price was $2,172, price is now $1,861 per person
$1,861
per person
found 1 day ago
Fairmont maybe an old hotel but it is well maintained hotel. With large rooms, great views of the skyline especially at night from our window. And Le Labo toiletries is a plus. Also Many great restaurants nearby
Reviewed on Aug 17, 2026
Don't see what you're looking for?
See all available trips from San Francisco to Oak Brook
View all tripsMore 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.