$49 Cheap flight deals from Oakland (SJC) to Chicago (CHI)

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This Weekend's Flight Deals from Oakland to Chicago

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, Apr 27 - Wed, May 8
SFO
San Francisco Intl.
MDW
Midway Intl.
$175 Roundtrip, found 3 days ago
$175
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Apr 27 from San Francisco Intl. to Midway Intl., returning Wed, May 8, priced at $175 found 3 days ago
Sat, Apr 27 - Sat, May 4
SFO
San Francisco Intl.
ORD
O'Hare Intl.
$360 Roundtrip, just found
$360
Roundtrip
just found
Select Alaska Airlines flight, departing Sat, Apr 27 from San Francisco Intl. to O'Hare Intl., returning Sat, May 4, priced at $360 just found
Sat, Apr 27 - Tue, Apr 30
OAK
Oakland Intl.
MDW
Midway Intl.
$393 Roundtrip, found 3 days ago
$393
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Apr 27 from Oakland Intl. to Midway Intl., returning Tue, Apr 30, priced at $393 found 3 days ago
Sat, Apr 27 - Mon, Apr 29
OAK
Oakland Intl.
ORD
O'Hare Intl.
$578 Roundtrip, found 3 hours ago
$578
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sat, Apr 27 from Oakland Intl. to O'Hare Intl., returning Mon, Apr 29, priced at $578 found 3 hours ago

Airfares from $49 One Way, $81 Round Trip from Oakland to Chicago

Prices starting at $81 for return flights and $49 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, May 15 - Tue, May 21
OAK
Oakland
ORD
Chicago
$81 Roundtrip, found 21 hours ago
$81
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Wed, May 15 from Oakland to Chicago, returning Tue, May 21, priced at $81 found 21 hours ago
Wed, May 15 - Tue, May 28
SJC
San Jose
ORD
Chicago
$106 Roundtrip, found 10 hours ago
$106
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Wed, May 15 from San Jose to Chicago, returning Tue, May 28, priced at $106 found 10 hours ago
Sat, May 18 - Sat, May 25
SFO
San Francisco
ORD
Chicago
$173 Roundtrip, just found
$173
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 18 from San Francisco to Chicago, returning Sat, May 25, priced at $173 just found
Tue, Jun 11 - Wed, Jun 12
SFO
San Francisco
ORD
Chicago
$173 Roundtrip, found 1 hour ago
$173
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Tue, Jun 11 from San Francisco to Chicago, returning Wed, Jun 12, priced at $173 found 1 hour ago
Tue, Sep 17 - Tue, Sep 24
SFO
San Francisco
ORD
Chicago
$196 Roundtrip, found 1 day ago
$196
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 17 from San Francisco to Chicago, returning Tue, Sep 24, priced at $196 found 1 day ago

Chicago economy flight packages

Prices and availability subject to change. Additional terms may apply.
Chicago Marriott Downtown Magnificent Mile
4.0-star property

Chicago Marriott Downtown Magnificent Mile

8.4/10 Very Good! (1,007 reviews)

Jun 15 - Jun 18

3 night stay

Oakland (OAK) to Chicago (ORD)

Spirit Airlines • Non-stop roundtrip • Coach
per person
This property was very nice and there were eating options and a great bar/lounge.

Reviewed on Apr 22, 2024

DoubleTree by Hilton Chicago - Magnificent Mile
4.0-star property

DoubleTree by Hilton Chicago - Magnificent Mile

8.6/10 Excellent! (2,153 reviews)

Jun 15 - Jun 18

3 night stay

Oakland (OAK) to Chicago (ORD)

Spirit Airlines • Non-stop roundtrip • Coach
per person
The garage was dark and dengue. The room description said city view. All you could see is a block wall. Orbitz description said the hotel had room service. They don’t. Web Site said no charge for early check in. They charged us $25 The room walls must be thin. We heard people talking from other rooms and in the hall. Anytime a neighbor used the restroom we could hear the water. Basically we got no sleep.

Reviewed on Apr 7, 2024

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

8.8/10 Excellent! (206 reviews)

Jun 15 - Jun 18

3 night stay

Oakland (OAK) to Chicago (ORD)

Spirit Airlines • Non-stop roundtrip • Coach
per person
Front desk and maintenance staff was amazing super succeeded our expectations i will return gor future dates

Reviewed on Feb 16, 2024

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More About Flying To Chicago from Oakland

Route Information for Flights from Oakland to Chicago

Origin Airport IATA Code
SJC
Destination Airport IATA Code
CHI
Distance
1842 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Air Canada, Austrian, Aer Lingus, Emirates, Asiana Airlines, Virgin Australia, Air New Zealand, United Airlines, Alaska Airlines, Qantas, China Southern Airlines, Royal Jordanian, SAS, Iberia, ANA, Brussels Airlines, Lufthansa, Singapore Airlines, Gulf Air, British Airways
Earliest Flight Arrival
1:30PM UTC
Latest Flight Arrival
1:23PM UTC

Flights from Oakland to Chicago

Oakland Airport Information

If you are searching for cheap flights from Oakland, Orbitz.com can help. The Oakland International Airport provides air service to the Oakland area and is located on Airport Drive, about 10 miles from downtown Oakland. Several major airlines provide service to the airport, including Alaska, Allegiant, ArkeFly, Delta, Hawaiian, JetBlue, Sata, Southwest, Spirit, US Airways, and Volaris. Orbitz.com can compare the rates on most of these carriers, so you can choose the best bargain before you purchase your tickets.

Parking Options Located at the Airport

The airport has several parking lots for you to choose from. Long-term parking is $22 a day, Short-term rates are $2 for 30 minutes with a daily rate of $32, economy parking is $16 per day, and premier parking, located right near the terminal, is $3 every 30 minutes with a daily maximum of $36.

Transportation to the Airport

Transportation to and from the airport is provided by shuttles, limos, taxis, car rentals, and the BART. Taxi service from downtown Oakland to the airport will cost around $28. Car rentals are a convenient way of getting to the airport, and Orbitz.com can find you the best rates from among the several different carriers.

Restaurants Located at the Airport

Restaurants located in the airport include Mua, Caffee Trieste, Marica, The Grand Tavern, Toast, Café Dejena, Yayu Ethiopian, and 360 Degrees Gourmet Burritos. These restaurants provide a wide variety of snack, dining, and breakfast options for travelers. Orbitz.com can find deals on transportation to the airport and cheap flights from Oakland when you are planning your next vacation.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Frequently asked questions

Are there non-stop flights from Oakland to Chicago?
There are 3 airlines flying nonstop from SFO to O’Hare Airport, so get ready to hit that “book” button. One of these top carriers will have your perfect flight:

  • United Airlines
  • American Airlines
  • Alaska Airlines

What is the shortest flight from Oakland to Chicago?
The quickest flight time from Oakland to Chicago is around 4 hours and 40 minutes. Grab your favorite tipple from the drink trolley, work on your travel itinerary or get to know your seat mate — you’ll have enough time on this medium-haul journey.
What airlines fly from Oakland to Chicago most frequently?
There are a few airlines offering frequent flights from SFO to O’Hare Airport, including United Airlines (UA). The preferred choice of many travelers, it operates 243 flights on this route each month. American Airlines (AA) will also fly you to your destination in style and comfort. Offering 126 flights every month between Oakland and Chicago, it’s another popular airline to look into.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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.