$86 Cheap flight deals from San Francisco (SJC) to Oak Park (CHI)

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

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.

Sun, Sep 13 - Tue, Sep 15
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$312 Roundtrip, found 11 hours ago
$312
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Sun, Sep 13 from San Francisco Intl. to O'Hare Intl., returning Tue, Sep 15, priced at $312 found 11 hours ago
Sat, Sep 12 - Mon, Sep 14
SFO
San Francisco Intl.
MDW
Midway Intl.
$373 Roundtrip, found 21 hours ago
$373
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Sat, Sep 12 from San Francisco Intl. to Midway Intl., returning Mon, Sep 14, priced at $373 found 21 hours ago
Sat, Sep 12 - Mon, Sep 14
OAK
Oakland Intl.
ORD
O'Hare Intl.
$427 Roundtrip, found 1 hour ago
$427
Roundtrip
found 1 hour ago
Select Bargain Flight flight, departing Sat, Sep 12 from Oakland Intl. to O'Hare Intl., returning Mon, Sep 14, priced at $427 found 1 hour ago
Sat, Sep 12 - Fri, Sep 18
OAK
Oakland Intl.
MDW
Midway Intl.
$513 Roundtrip, found 22 hours ago
$513
Roundtrip
found 22 hours ago
Select Southwest Airlines flight, departing Sat, Sep 12 from Oakland Intl. to Midway Intl., returning Fri, Sep 18, priced at $513 found 22 hours ago

Airfares from $86 One Way, $165 Round Trip from San Francisco to Oak Park

Prices starting at $165 for return flights and $86 for one-way flights to Oak Park 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, Oct 13 - Tue, Oct 20
SFO
San Francisco
ORD
Chicago
$165 Roundtrip, found 17 hours ago
$165
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Tue, Oct 13 from San Francisco to Chicago, returning Tue, Oct 20, priced at $165 found 17 hours ago
Thu, Oct 22 - Mon, Oct 26
SJC
San Jose
ORD
Chicago
$241 Roundtrip, found 15 hours ago
$241
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Thu, Oct 22 from San Jose to Chicago, returning Mon, Oct 26, priced at $241 found 15 hours ago
Wed, Nov 11 - Tue, Nov 17
SFO
San Francisco
MDW
Chicago
$256 Roundtrip, found 22 hours ago
$256
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Wed, Nov 11 from San Francisco to Chicago, returning Tue, Nov 17, priced at $256 found 22 hours ago
Tue, Sep 29 - Tue, Oct 6
OAK
Oakland
ORD
Chicago
$257 Roundtrip, found 6 days ago
$257
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Sep 29 from Oakland to Chicago, returning Tue, Oct 6, priced at $257 found 6 days ago
Fri, Oct 2 - Sat, Oct 3
OAK
Oakland
ORD
Chicago
$282 Roundtrip, found 4 days ago
$282
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Fri, Oct 2 from Oakland to Chicago, returning Sat, Oct 3, priced at $282 found 4 days ago

Oak Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Chicago Lake Shore Hotel
3.0-star property

Chicago Lake Shore Hotel

7/10 Good! (1,004 reviews)

Nov 3 - Nov 9

6 night stay

San Francisco (SFO) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to San Francisco (SFO)

Frontier Airlines • Coach
Price was $889, price is now $680 per person
$680
per person
found 16 hours ago
Internet connection sucked and was not informed of security deposit until we got there

Reviewed on Sep 8, 2026

Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

9.2/10 Wonderful! (561 reviews)

Oct 16 - Oct 20

4 night stay

San Jose (SJC) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to San Jose (SJC)

Alaska Airlines • Coach
Save 100% on your flight
Price was $1,762, price is now $1,176 per person
$1,176
per person
found 12 hours ago
The pool & jacuzzi was perfect, this hotel is beautiful

Reviewed on Sep 7, 2026

The Talbott, Autograph Collection
4.5-star property

The Talbott, Autograph Collection

9.4/10 Exceptional! (165 reviews)

Nov 6 - Nov 9

3 night stay

San Francisco (SFO) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to San Francisco (SFO)

Frontier Airlines • Coach
Price was $953, price is now $691 per person
$691
per person
found 1 day ago
Old,

Reviewed on Sep 8, 2026

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More About Flying To Oak Park from San Francisco

Route Information for Flights from San Francisco to Oak Park

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

San Francisco to Oak Park

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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.