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	$260	Southwest Nonstop 5 hr Sun, Jan 11 — Tue, Jan 20	The cheapest round-trip flight from Chicago to Oakland is currently $260
Cheapest one-way flight	$130	Southwest Nonstop 5 hr Sat, Jan 31	The cheapest one-way flight from Chicago to Oakland is currently $130
Cheapest nonstop flights	$269	Southwest Nonstop 5 hr Thu, Jan 8 — Wed, Jan 14	The cheapest nonstop round-trip flight from Chicago to Oakland is currently $269
Last-minute weekend getaway	$402	Delta 1 stop 7 hr Sat, Nov 22 — Mon, Nov 24	The cheapest last-minute weekend getaway from Chicago to Oakland is currently $402
Cheapest business class flights	$997	Alaska 1 stop 22 hr Mon, Feb 2 — Mon, Feb 9	The cheapest business class round-trip flight from Chicago to Oakland is currently $997

Fastest flight	4 hr 35 min	The fastest nonstop flight from Chicago to Oakland takes 4 hr 35 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 January. The most expensive month to fly is typically November.

January Cheapest	Typical prices: $145–305
November Most expensive	Typical prices: $280–550

Popular airlines from Chicago to Oakland

Southwest

Nonstop

from $260

Typical price: $255–495

7 weekly nonstop flights

MDW - OAK Every day

3570 weekly connecting flights

MDW, ORD - OAK Every day
Delta

from $279

Typical price: $325–830

300 weekly connecting flights

MDW, ORD - OAK Every day
Alaska

from $279

Typical price: $305–650

92 weekly connecting flights

ORD - OAK Every day

Popular airports near Chicago

Chicago O'Hare International Airport (ORD)

Chicago United States 31 min 16 mi
Chicago Midway International Airport (MDW)

Chicago United States 26 min 9 mi
Milwaukee Mitchell International Airport (MKE)

Milwaukee United States 1 hr 28 min 75 mi
Indianapolis International Airport (IND)

Indianapolis United States 2 hr 58 min 165 mi

Popular airports near Oakland

Oakland International 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 48 min 35 mi
Sacramento International Airport (SMF)

Sacramento United States 1 hr 26 min 71 mi

Frequently asked questions about flying from Chicago to Oakland

When are the cheapest days to fly from Chicago to Oakland?

The cheapest flights from Chicago to Oakland are usually in January. Typical ticket prices in January range from $145 to $305.

Which airlines provide the cheapest flights from Chicago to Oakland?

The cheapest round-trip flight from Chicago to Oakland recently found on Google Flights was with Southwest from $260. The cheapest one-way flight was with Southwest from $130.

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

The cheapest Southwest flight from Chicago to Oakland is $260, flying from Jan 11 to Jan 20.
The cheapest Delta flight from Chicago to Oakland is $279, flying from Dec 6 to Dec 13.
The cheapest Alaska flight from Chicago to Oakland is $279, flying from Jan 24 to Jan 31.

What are the cheapest flights from Chicago to Oakland?

The cheapest round-trip flight from Chicago to Oakland starts at $260 from Sun, Jan 11 to Tue, Jan 20. The cheapest one-way flight starts at $130 and departs on Sat, Jan 31.

How long does it take to fly from Chicago to Oakland?

4 hr 35 min is the shortest flight time from Chicago to Oakland.

When should you fly to Oakland, United States?

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.

How do I find cheap dates to fly from Chicago to Oakland?

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 is the best airline to fly from Chicago to Oakland?

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 7 nonstop flights and 3,570 connecting flights per week. Southwest flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Oakland International Airport (OAK) .

Other popular airlines flying from Chicago to Oakland are:

Delta offers 300 connecting flights per week. Delta flies from Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) to Oakland International Airport (OAK) .
Alaska offers 92 connecting flights per week. Alaska flies from Chicago O'Hare International Airport (ORD) to Oakland International Airport (OAK) .

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

Which airlines provide the cheapest flights from Chicago to Oakland?

The cheapest round-trip flight from Chicago to Oakland recently found on Google Flights was with Southwest from $260. The cheapest one-way flight was with Southwest from $130.

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

The cheapest Southwest flight from Chicago to Oakland is $260, flying from Jan 11 to Jan 20.
The cheapest Delta flight from Chicago to Oakland is $279, flying from Dec 6 to Dec 13.
The cheapest Alaska flight from Chicago to Oakland is $279, flying from Jan 24 to Jan 31.

Which airlines have direct flights from Chicago to Oakland?

Southwest flies direct from Chicago to Oakland.

There are 7 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.

Which airline provides the cheapest last-minute getaway flight from Chicago to Oakland?

The cheapest last-minute deal between Chicago and Oakland at price $402 is offered by Delta from Sat, Nov 22 to Mon, Nov 24.

Which airlines have direct flights from Chicago to Oakland?

Southwest flies direct from Chicago to Oakland.

There are 7 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.

When are direct flights from Chicago to Oakland available?

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

What are the cheapest direct flights from Chicago to Oakland?

The cheapest direct (nonstop) round-trip flights between Chicago and Oakland start at $269 from Thu, Jan 8 to Wed, Jan 14 with Southwest.

How can I find nonstop flights from Chicago to Oakland?

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.

What are the cheapest business class flights from Chicago to Oakland?

The cheapest business class round-trip flights between Chicago and Oakland start at $997 from Mon, Feb 2 to Mon, Feb 9 with Alaska.

What are the cheapest economy class flights from Chicago to Oakland?

The cheapest economy class round-trip flights between Chicago and Oakland start at $260 from Sun, Jan 11 to Tue, Jan 20.

How can I book business class trips from Chicago to Oakland?

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.

Are there any last-minute deals from Chicago to Oakland next weekend?

The best last-minute getaway deal for the next weekend between Chicago and Oakland starts at $402 from Sat, Nov 22 to Mon, Nov 24 with Delta.

Which airline provides the cheapest last-minute getaway flight from Chicago to Oakland?

The cheapest last-minute deal between Chicago and Oakland at price $402 is offered by Delta from Sat, Nov 22 to Mon, Nov 24.

How can I find last-minute flight deals from Chicago to Oakland?

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.