Find Cheap Flights from Chicago to Oakland (CHI - OAK)

Flights overview

Useful information for finding cheap flights from Chicago to Oakland and booking your next trip

Cheapest round-trip flights	$261	Southwest Nonstop 5 hr Thu, May 28 — Wed, Jun 3	The cheapest round-trip flight from Chicago to Oakland is currently $261
Cheapest one-way flight	$119	Southwest Nonstop 5 hr Tue, Jun 2	The cheapest one-way flight from Chicago to Oakland is currently $119
Cheapest nonstop flights	$335	Southwest Nonstop 5 hr Thu, Jul 30 — Thu, Aug 6	The cheapest nonstop round-trip flight from Chicago to Oakland is currently $335
Last-minute weekend getaway	$482	Alaska 1 stop 8 hr Sat, May 9 — Sun, May 10	The cheapest last-minute weekend getaway from Chicago to Oakland is currently $482
Cheapest business class flights	$993	Alaska 1 stop 12 hr Sat, May 30 — Sat, Jun 6	The cheapest business class round-trip flight from Chicago to Oakland is currently $993

Fastest flight	4 hr 30 min	The fastest nonstop flight from Chicago to Oakland takes 4 hr 30 min
Nonstop flights	Every day	There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from Chicago to Oakland is typically August. The most expensive month to fly is typically December.

August Cheapest	Typical prices: $185–350
December Most expensive	Typical prices: $285–560

Popular airlines from Chicago to Oakland

Southwest

Nonstop

from $261

Typical price: $255–510

12 weekly nonstop flights

MDW - OAK Every day

3503 weekly connecting flights

MDW, ORD - OAK Every day
Delta

from $355

Typical price: $365–940

120 weekly connecting flights

MDW, ORD - OAK Every day
Alaska

from $313

Typical price: $295–660

116 weekly connecting flights

ORD - OAK Every day

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 26 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 25 min 9 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 23 min 75 mi
Indianapolis International Airport (IND)

Indianapolis United States 2 hr 58 min 165 mi

Popular airports near Oakland

Oakland San Francisco Bay Airport (OAK)

Oakland United States 15 min 6 mi
San Francisco International Airport (SFO)

San Francisco United States 30 min 14 mi
San Jose Mineta International Airport (SJC)

San Jose United States 47 min 35 mi
Sacramento International Airport (SMF)

Sacramento United States 1 hr 27 min 71 mi

Frequently asked questions about flying from Chicago to Oakland

The cheapest flights from Chicago to Oakland are usually in August. Typical ticket prices in August range from $185 to $350.

The cheapest round-trip flight from Chicago to Oakland recently found on Google Flights was with Southwest from $261. The cheapest one-way flight was with Southwest from $119.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from Chicago to Oakland is $261, flying from May 28 to Jun 3.
The cheapest Delta flight from Chicago to Oakland is $355, flying from Jul 2 to Jul 11.
The cheapest Alaska flight from Chicago to Oakland is $313, flying from May 30 to Jun 6.

The cheapest round-trip flight from Chicago to Oakland starts at $261 from Thu, May 28 to Wed, Jun 3. The cheapest one-way flight starts at $119 and departs on Tue, Jun 2.

4 hr 30 min is the shortest flight time from Chicago to Oakland.

Oakland is a year-round destination with a mild climate. Popular times to visit include the warmest months (May–Oct). Jack London Square is the site of many city events, including a weekly farmers’ market (Sun). Art + Soul Oakland (Aug) sees art, dance, music and kids’ events, plus food and craft vendors. The Eat Real Festival (Sep) offers cooking demonstrations, street food and live music in Jack London Square.

It's easy to use Google Flights to find the cheapest days to fly from Chicago to Oakland.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.

What counts as the best airline for your flights from Chicago to Oakland really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Chicago to Oakland.

In terms of nonstop flights, Southwest is the most popular. Southwest offers 12 nonstop flights and 3,503 connecting flights per week. Southwest flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Oakland San Francisco Bay Airport (OAK) .

Other popular airlines flying from Chicago to Oakland are:

Delta offers 120 connecting flights per week. Delta flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Oakland San Francisco Bay Airport (OAK) .
Alaska offers 116 connecting flights per week. Alaska flies from Chicago O'Hare International Airport (ORD) to Oakland San Francisco Bay Airport (OAK) .

The number of connecting flights refers to distinct flights with at least one stop between Chicago and Oakland.

The cheapest round-trip flight from Chicago to Oakland recently found on Google Flights was with Southwest from $261. The cheapest one-way flight was with Southwest from $119.

Some of the cheapest round-trip deals we found with different airlines:

The cheapest Southwest flight from Chicago to Oakland is $261, flying from May 28 to Jun 3.
The cheapest Delta flight from Chicago to Oakland is $355, flying from Jul 2 to Jul 11.
The cheapest Alaska flight from Chicago to Oakland is $313, flying from May 30 to Jun 6.

Southwest flies direct from Chicago to Oakland.

There are 12 Southwest direct flights from Chicago to Oakland per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

The cheapest last-minute deal between Chicago and Oakland at price $482 is offered by Alaska from Sat, May 9 to Sun, May 10.

Southwest flies direct from Chicago to Oakland.

There are 12 Southwest direct flights from Chicago to Oakland per week. Flights are available every day.

Use the Stops filter while searching for flights, to see only nonstop options in your results.

There are direct flights from Chicago to Oakland on a daily basis.

The cheapest direct (nonstop) round-trip flights between Chicago and Oakland start at $335 from Thu, Jul 30 to Thu, Aug 6 with Southwest.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Chicago to Oakland, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.

The cheapest business class round-trip flights between Chicago and Oakland start at $993 from Sat, May 30 to Sat, Jun 6 with Alaska.

The cheapest economy class round-trip flights between Chicago and Oakland start at $261 from Thu, May 28 to Wed, Jun 3.

To book business class trips from Chicago to Oakland, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.

The best last-minute getaway deal for the next weekend between Chicago and Oakland starts at $482 from Sat, May 9 to Sun, May 10 with Alaska.

The cheapest last-minute deal between Chicago and Oakland at price $482 is offered by Alaska from Sat, May 9 to Sun, May 10.

To find last-minute flight deals from Chicago to Oakland, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.