$67 Find Cheap Flights from Oakland to Chicago

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Find cheap flights from Oakland to Chicago starting at $67.

Book one-way or return flights from Oakland to Chicago from as little as $67. Choose from the popular airlines below and book your flight today!

One way
Round-trip

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Searching for the best last minute flight from Oakland to Chicago? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Oakland to Chicago. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Find cheap airlines flights from Oakland to Chicago

View airlines operating flights from Oakland to Chicago. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Spirit Airlines

From $67

Sun Country Airlines

From $88

Delta Air Lines

From $92

Alaska Airlines

From $100

Southwest Airlines

From $144

Hawaiian Airlines

From $509

American Airlines

From $1,221

ANA airlines

Find more flights and airlines

Find cheap flights from Oakland to Chicago by different airports

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Oakland to Chicago.

Cheapest
OAK
21:29
7h 1m
1 transfer
ORD
06:30
Oakland International Airport - O'Hare International Airport
Tue, May 14Spirit Airlines
$67
OAK
21:29
12h 7m
1 transfer
MDW
11:36
Oakland International Airport - Midway International Airport
Tue, May 14Spirit Airlines
$79
OAK
05:30
13h 38m
1 transfer
RFD
21:08
Oakland International Airport - Chicago Rockford International Airport
Thu, May 9Spirit Airlines
$185
OAK
05:30
13h 38m
1 transfer
RFD
21:08
Oakland International Airport - Chicago Rockford International Airport
Thu, May 9Spirit Airlines
$185
Find More Flights

Frequently Asked Questions

When are flight tickets from Oakland (OAK) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Oakland to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
How much do flights from Oakland (OAK) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around $365.
How long does it take to fly from Oakland (OAK) to Chicago (CHI) and what is the distance?
It takes around 5 hours 22 minutes to fly from Oakland (OAK) to Chicago (CHI).
What is the transportation method from the main airport to downtown in Chicago?
- The distance from O'Hare International Airport to downtown is about 25km. It takes about 40 minutes by taxi.
- The distance from Midway International Airport to downtown is about 14km. It takes about 30 minutes by taxi.
What are the most popular airlines that fly from Oakland (OAK) to Chicago (CHI)?
Airlines with flights from Oakland (OAK) to Chicago (CHI): Southwest Airlines.

How to find a cheap flight from Oakland to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Oakland to Chicago. Book your flights at the right time and save more.

Book Early

Once prices are gone, they're gone. Lock in deals while you can!

Compare Flight Prices

Compare prices on travel agency and airline websites.

Look Out for Deals

Check airline and travel agency websites for latest flight deals

Check One-way Fares

Buying two cheap one-way flights can sometimes be a better deal than a round-trip.

Try Different Dates

Flying during the week, early in the morning, or late at night can help save money.

Use the Trip.com App

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Oakland to Chicago Flight Information

Cheapest nonstop flight price	$67
Cheapest round-trip ticket price	$276
Off-season for travel	February
Peak season for travel	October
Flight distance	2,969.56km
Average flight time	5 hours 22 minutes
Popular airline	Alaska Airlines