$107 Cheap flight deals from Oakland (SJC) to Oak Park (CHI)

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This Weekend's Flight Deals from Oakland 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.

Sat, Jul 18 - Tue, Jul 21
SFO
San Francisco Intl.
MDW
Midway Intl.
$369 Roundtrip, found 8 hours ago
$369
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, Jul 18 from San Francisco Intl. to Midway Intl., returning Tue, Jul 21, priced at $369 found 8 hours ago
Fri, Jul 17 - Tue, Jul 21
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$369 Roundtrip, just found
$369
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Jul 17 from San Francisco Intl. to O'Hare Intl., returning Tue, Jul 21, priced at $369 just found
Sat, Jul 18 - Thu, Jul 23
SJC
Norman Y. Mineta San Jose Intl.
ORD
O'Hare Intl.
$509 Roundtrip, found 23 hours ago
$509
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Sat, Jul 18 from Norman Y. Mineta San Jose Intl. to O'Hare Intl., returning Thu, Jul 23, priced at $509 found 23 hours ago
Sat, Jul 18 - Tue, Jul 28
SFO
San Francisco Intl.
RFD
Greater Rockford
$553 Roundtrip, found 2 days ago
$553
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Jul 18 from San Francisco Intl. to Greater Rockford, returning Tue, Jul 28, priced at $553 found 2 days ago

Airfares from $107 One Way, $213 Round Trip from Oakland to Oak Park

Prices starting at $213 for return flights and $107 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, Sep 8 - Sat, Sep 12
OAK
Oakland
MDW
Chicago
$213 Roundtrip, found 6 days ago
$213
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Sep 8 from Oakland to Chicago, returning Sat, Sep 12, priced at $213 found 6 days ago
Mon, Aug 10 - Thu, Aug 13
SFO
San Francisco
ORD
Chicago
$213 Roundtrip, found 3 days ago
$213
Roundtrip
found 3 days ago
Select United flight, departing Mon, Aug 10 from San Francisco to Chicago, returning Thu, Aug 13, priced at $213 found 3 days ago
Tue, Aug 11 - Wed, Aug 19
SFO
San Francisco
ORD
Chicago
$213 Roundtrip, found 4 days ago
$213
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Aug 11 from San Francisco to Chicago, returning Wed, Aug 19, priced at $213 found 4 days ago
Thu, Sep 24 - Tue, Sep 29
SFO
San Francisco
MDW
Chicago
$234 Roundtrip, found 4 days ago
$234
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, Sep 24 from San Francisco to Chicago, returning Tue, Sep 29, priced at $234 found 4 days ago
Tue, Sep 8 - Sat, Sep 12
SJC
San Jose
MDW
Chicago
$237 Roundtrip, found 1 hour ago
$237
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Tue, Sep 8 from San Jose to Chicago, returning Sat, Sep 12, priced at $237 found 1 hour ago

Oak Park economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

8.2/10 Very Good! (2,809 reviews)

Sep 2 - Sep 6

4 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,119, price is now $749 per person
$749
per person
found 1 day ago
We stayed for our first time in Chicago. Loved the area. The hotel is clean and well maintained. The staff is amazing. Thank you, Marena for welcoming us.

Reviewed on Jul 14, 2026

Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

9.2/10 Wonderful! (512 reviews)

Sep 2 - Sep 6

4 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,400, price is now $929 per person
$929
per person
found 1 day ago
We booked a two bedroom unit, but the unit clearly wasn't intended for a 2 bedroom. It was obviously a sitting area or something with a bed squeezed in. There was no vent so it made it impossible to shut the door, but then it was open to the living space and a full wall of windows. In addition, they list housekeeping as an amenity, and advertise one day or long term stays, however, for our 4 night stay, this didn't get housekeeping services. Meaning we had to get towels and coffee each day from the front desk, had piles of trash from cooking and such, and a heap of dirty towels from the week. Staff was friendly, but not really provided agency or capacity to do anything to fix the experience. Even a request for a fan to try to cool the space was impossible for them to solve (although they certainly had one for the front desk to keep staff comfortable).

Reviewed on Jul 14, 2026

Level Chicago - River North
4.0-star property

Level Chicago - River North

9.2/10 Wonderful! (1,020 reviews)

Sep 2 - Sep 6

4 night stay

Oakland (OAK) to Chicago (ORD)

Southwest Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,397, price is now $929 per person
$929
per person
found 1 day ago
Clean rooms, nice pool, location great

Reviewed on Jul 12, 2026

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Oak Park first class flight packages

Price found within the past 48 hours. Click for updated prices.
Thompson Chicago, by Hyatt
4.5-star property

Thompson Chicago, by Hyatt

9.2/10 Wonderful! (1,388 reviews)

Sep 3 - Sep 8

5 night stay

Oakland (OAK) to Chicago (ORD)

Alaska Airlines • Non-stop roundtrip • FirstClass
Price was $2,240, price is now $1,874 per person
$1,874
per person
found 16 hours ago
Beautiful hotel with nice city views. Friendly staff. So many hidden fees, doubled the cost.

Reviewed on Jul 12, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,566 reviews)

Sep 3 - Sep 8

5 night stay

Oakland (OAK) to Chicago (ORD)

Alaska Airlines • Non-stop roundtrip • FirstClass
Price was $2,654, price is now $2,055 per person
$2,055
per person
found 16 hours ago
Very clean nice workers and amazing views

Reviewed on Jul 14, 2026

The Langham, Chicago
5.0-star property

The Langham, Chicago

9.8/10 Exceptional! (1,003 reviews)

Sep 3 - Sep 8

5 night stay

Oakland (OAK) to Chicago (ORD)

Alaska Airlines • Non-stop roundtrip • FirstClass
Price was $3,561, price is now $2,827 per person
$2,827
per person
found 16 hours ago
The Langham was one of my favorite hotels I've ever stayed at. The shower was incredible, the bed felt like heaven and the overall room set-up was amazing. I especially loved the vanity! I also highly recommend the hotel restaurant for breakfast. I had breakfast there every day of my stay and it was delicious! Can't wait to go back.

Reviewed on Jul 13, 2026

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More About Flying To Oak Park from Oakland

Route Information for Flights from Oakland to Oak Park

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

Oakland 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.