Cheap Flights from Oakland to Chicago

Popular airlines from Oakland Intl. Airport (OAK) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Oakland to Chicago (OAK-ORD)

Prices were available within the past 7 days and start at for one-way flights and S$1,536 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$1,536 Return, found 13 hours ago
S$1,536
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$1,536 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$1,602 Return, found 13 hours ago
S$1,602
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$1,602 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$1,742 Return, found 13 hours ago
S$1,742
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$1,742 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$2,024 Return, found 13 hours ago
S$2,024
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$2,024 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$2,057 Return, found 13 hours ago
S$2,057
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$2,057 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$2,079 Return, found 13 hours ago
S$2,079
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$2,079 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$2,097 Return, found 13 hours ago
S$2,097
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$2,097 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$2,125 Return, found 13 hours ago
S$2,125
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$2,125 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$2,134 Return, found 13 hours ago
S$2,134
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$2,134 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$2,148 Return, found 13 hours ago
S$2,148
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$2,148 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$2,156 Return, found 13 hours ago
S$2,156
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$2,156 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$2,166 Return, found 13 hours ago
S$2,166
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$2,166 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$2,203 Return, found 13 hours ago
S$2,203
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$2,203 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$2,224 Return, found 13 hours ago
S$2,224
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$2,224 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$2,233 Return, found 13 hours ago
S$2,233
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$2,233 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$2,281 Return, found 13 hours ago
S$2,281
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$2,281 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$2,299 Return, found 13 hours ago
S$2,299
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$2,299 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$2,301 Return, found 13 hours ago
S$2,301
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$2,301 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$2,302 Return, found 13 hours ago
S$2,302
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$2,302 found 13 hours ago
Delta
Sun, 30 Nov - Wed, 3 Dec
OAK
Oakland
ORD
Chicago
S$2,309 Return, found 13 hours ago
S$2,309
Return
found 13 hours ago
Select Delta flight, departing Sun, 30 Nov from Oakland to Chicago, returning Wed, 3 Dec, priced at S$2,309 found 13 hours ago

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Find the cheapest month to fly from Oakland (OAK) to Chicago (ORD)

January is typically the cheapest month to fly

From S$138 - S$417 per traveller.
Oakland to Chicago route information
Origin airport
Oakland Intl.
Destination airport
O'Hare Intl.
Airlines serving
Delta
Return price
S$1,535
Distance
2929 km
Average flight time
7 hours 50 mins

Perfect flights from Oakland to Chicago

Your Journey from Oakland to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Oakland to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta. Our selection of flights from Oakland Intl. to O'Hare Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Oakland to Chicago Flights

Experience the joy of finding cheap flights from Oakland Intl. to O'Hare Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares and roundtrip prices from S$1,536*.
 

Pre-Flight Essentials

Ensure a smooth journey from Oakland to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Oakland to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Oakland to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Oakland to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Oakland to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from OAK to O'Hare Intl. Airport (ORD)?
If you're planning on travelling between Oakland Intl. Airport and ORD, round-trip journeys start from S$1,536. This price is based on fares listed within the last 7 days on Expedia for flights departing within the next year, so don't wait around. Book today and save yourself money and time. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from OAK to ORD?
Each air carrier has its own set of terms and conditions. If you decide to cancel your getaway, visit our Customer Service Portal.
How do I find cheap flights from OAK to O'Hare Intl. Airport (ORD) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Oakland Intl. Airport (OAK) to O'Hare Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Oakland Intl. Airport to O'Hare Airport?
Around 3,000 kilometres separates Oakland and Chicago, so pack something to help you fill in a few hours. That latest bestseller you're eager to read will be just the ticket.
Which airlines fly direct from Oakland Intl. Airport to ORD?
If you want to fly straight from OAK to O'Hare Airport, you'll have to book a flight with at least one stop. Unfortunately, there are no airlines that fly directly between these airports.
Are Oakland Intl. Airport (OAK) to O'Hare Airport flight tickets cheaper when they're purchased at the last minute?
Last-minute bookings from Oakland Intl. Airport (OAK) to O'Hare Airport can be hit-or-miss. It is possible to find a bargain, but then again, you could miss out entirely! If you'd prefer to play it safe and start your trip planning early on, Expedia compares flight deals up to 12 months in advance. Just keep in mind that not all airlines publish their prices so far in advance. Our top tip? Check back often as updates are made frequently.

Explore a world of travel with Expedia

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*Available to Expedia members.