$124 Cheap flight deals from Chicago (CHI) to Pittsburg (OAK)

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This Weekend's Flight Deals from Chicago to Pittsburg

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.

Fri, Jul 10 - Sat, Jul 11
ORD
O'Hare Intl.
OAK
Oakland Intl.
$432 Roundtrip, found 10 hours ago
$432
Roundtrip
found 10 hours ago
Select Bargain Flight flight, departing Fri, Jul 10 from O'Hare Intl. to Oakland Intl., returning Sat, Jul 11, priced at $432 found 10 hours ago

Airfares from $124 One Way, $269 Round Trip from Chicago to Pittsburg

Prices starting at $269 for return flights and $124 for one-way flights to Pittsburg were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Aug 13 - Sat, Aug 15
MDW
Chicago
OAK
Oakland
$269 Roundtrip, found 3 days ago
$269
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Aug 13 from Chicago to Oakland, returning Sat, Aug 15, priced at $269 found 3 days ago
Wed, Dec 2 - Thu, Dec 3
ORD
Chicago
OAK
Oakland
$273 Roundtrip, found 5 days ago
$273
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Wed, Dec 2 from Chicago to Oakland, returning Thu, Dec 3, priced at $273 found 5 days ago
Thu, Aug 13 - Sat, Aug 15
ORD
Chicago
OAK
Oakland
$279 Roundtrip, found 3 days ago
$279
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Aug 13 from Chicago to Oakland, returning Sat, Aug 15, priced at $279 found 3 days ago
Tue, Aug 11 - Tue, Aug 18
ORD
Chicago
OAK
Oakland
$289 Roundtrip, found 2 days ago
$289
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Aug 11 from Chicago to Oakland, returning Tue, Aug 18, priced at $289 found 2 days ago
Wed, Sep 9 - Mon, Sep 14
ORD
Chicago
OAK
Oakland
$290 Roundtrip, found 3 days ago
$290
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Sep 9 from Chicago to Oakland, returning Mon, Sep 14, priced at $290 found 3 days ago

Pittsburg economy flight packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Berkeley Marina
4.0-star property

DoubleTree by Hilton Hotel Berkeley Marina

8.2/10 Very Good! (4,799 reviews)

Aug 15 - Aug 18

3 night stay

Chicago (CHI) to Oakland (OAK)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $831, price is now $552 per person
$552
per person
found 23 hours ago
Great stay for a family of 9. Loved the rooms!

Reviewed on Jul 6, 2026

Claremont Resort & Club
5.0-star property

Claremont Resort & Club

9/10 Wonderful! (1,023 reviews)

Aug 15 - Aug 19

4 night stay

Chicago (ORD) to Oakland (OAK)

American Airlines • Coach

Oakland (OAK) to Chicago (ORD)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,964, price is now $1,127 per person
$1,127
per person
found 1 hour ago

White House Napa
4.0-star property

White House Napa

9.2/10 Wonderful! (630 reviews)

Aug 20 - Aug 23

3 night stay

Chicago (CHI) to Oakland (OAK)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,316, price is now $877 per person
$877
per person
found 1 day ago
If you’re looking for an upmarket bed and breakfast this is a good spot

Reviewed on Jul 5, 2026

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Pittsburg first class flight packages

Price found within the past 48 hours. Click for updated prices.
Sonesta Emeryville - San Francisco Bay Bridge
3.0-star property

Sonesta Emeryville - San Francisco Bay Bridge

8.6/10 Excellent! (1,546 reviews)

Aug 26 - Aug 31

5 night stay

Chicago (ORD) to Oakland (OAK)

American Airlines • FirstClass

Oakland (OAK) to Chicago (ORD)

Frontier Airlines • FirstClass
Price was $1,203, price is now $1,114 per person
$1,114
per person
found 1 day ago
Staff was friendly - and some were particularly helpful including a maintenance worker who literally helped us patch our smashed window with some cardboard. Our room had a cracked window and shoe prints in the bathroom upon our arrival. While the room was otherwise clean enough and quiet, the shoe prints to start were quite a turnoff. Most of the property still looks in pretty good condition but the elevator (especially the buttons) appear quite worn. Worst part was - the $25/night parking. It wasn't as if parking was scarce - so the charge is already steep. Not sure (besides just charging people) what the fee is for because there is no security. Our car was broken into overnight while parked in the compound. It had its back to a fence and as in the front of the hotel within view of our room. I have stayed at this hotel probably 7 times (four times for personal/family travel) but I think this time may have been my last.

Reviewed on Jul 6, 2026

Courtyard San Francisco Larkspur Landing/Marin County
3.0-star property

Courtyard San Francisco Larkspur Landing/Marin County

8.8/10 Excellent! (834 reviews)

Aug 26 - Aug 31

5 night stay

Chicago (ORD) to Oakland (OAK)

American Airlines • FirstClass

Oakland (OAK) to Chicago (ORD)

Frontier Airlines • FirstClass
Price was $1,541, price is now $1,421 per person
$1,421
per person
found 1 day ago
Convenient, comfortable, clean, love the pool, very pretty environment, most of staff very helpful.

Reviewed on Jun 29, 2026

Residence Inn by Marriott Oakland Downtown
3.5-star property

Residence Inn by Marriott Oakland Downtown

9.4/10 Exceptional! (545 reviews)

Aug 26 - Aug 31

5 night stay

Chicago (ORD) to Oakland (OAK)

American Airlines • FirstClass

Oakland (OAK) to Chicago (ORD)

Frontier Airlines • FirstClass
Price was $1,264, price is now $1,216 per person
$1,216
per person
found 1 day ago

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More About Flying To Pittsburg from Chicago

Route Information for Flights from Chicago to Pittsburg

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

Chicago to Pittsburg

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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.