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

Flights overview

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

Cheapest round-trip flights	$261	Southwest 1 stop 7 hr Thu, May 28 — Wed, Jun 3	The cheapest round-trip flight from Oakland to Chicago is currently $261
Cheapest one-way flight	$119	Southwest Nonstop 5 hr Wed, May 27	The cheapest one-way flight from Oakland to Chicago is currently $119
Cheapest nonstop flights	$335	Southwest Nonstop 5 hr Thu, Jul 9 — Wed, Jul 15	The cheapest nonstop round-trip flight from Oakland to Chicago is currently $335
Last-minute weekend getaway	$482	Alaska 1 stop 8 hr Sat, May 9 — Mon, May 11	The cheapest last-minute weekend getaway from Oakland to Chicago is currently $482
Cheapest business class flights	$993	Alaska 1 stop 7 hr Sat, May 30 — Sat, Jun 6	The cheapest business class round-trip flight from Oakland to Chicago is currently $993

Fastest flight	4 hr 5 min	The fastest nonstop flight from Oakland to Chicago takes 4 hr 5 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 Oakland to Chicago is typically August. The most expensive month to fly is typically November.

August Cheapest	Typical prices: $180–340
November Most expensive	Typical prices: $285–580

Popular airlines from Oakland to Chicago

Southwest

Nonstop

from $261

Typical price: $255–520

12 weekly nonstop flights

OAK - MDW Every day

3518 weekly connecting flights

OAK - MDW, ORD Every day
Delta

from $355

Typical price: $375–950

157 weekly connecting flights

OAK - MDW, ORD Every day
Alaska

from $313

Typical price: $295–660

118 weekly connecting flights

OAK - ORD Every day

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

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

Frequently asked questions about flying from Oakland to Chicago

The cheapest flights from Oakland to Chicago are usually in August. Typical ticket prices in August range from $180 to $340.

The cheapest round-trip flight from Oakland to Chicago 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 Oakland to Chicago is $261, flying from May 28 to Jun 3.
The cheapest Delta flight from Oakland to Chicago is $355, flying from Jul 11 to Jul 20.
The cheapest Alaska flight from Oakland to Chicago is $313, flying from May 30 to Jun 6.

The cheapest round-trip flight from Oakland to Chicago starts at $261 from Thu, May 28 to Wed, Jun 3. The cheapest one-way flight starts at $119 and departs on Wed, May 27.

4 hr 5 min is the shortest flight time from Oakland to Chicago.

Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.

It's easy to use Google Flights to find the cheapest days to fly from Oakland to Chicago.
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 Oakland to Chicago 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 Oakland to Chicago.

In terms of nonstop flights, Southwest is the most popular. Southwest offers 12 nonstop flights and 3,518 connecting flights per week. Southwest flies from Oakland San Francisco Bay Airport (OAK) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from Oakland to Chicago are:

Delta offers 157 connecting flights per week. Delta flies from Oakland San Francisco Bay Airport (OAK) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
Alaska offers 118 connecting flights per week. Alaska flies from Oakland San Francisco Bay Airport (OAK) to Chicago O'Hare International Airport (ORD) .

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

The cheapest round-trip flight from Oakland to Chicago 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 Oakland to Chicago is $261, flying from May 28 to Jun 3.
The cheapest Delta flight from Oakland to Chicago is $355, flying from Jul 11 to Jul 20.
The cheapest Alaska flight from Oakland to Chicago is $313, flying from May 30 to Jun 6.

Southwest flies direct from Oakland to Chicago.

There are 12 Southwest direct flights from Oakland to Chicago 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 Oakland and Chicago at price $482 is offered by Alaska from Sat, May 9 to Mon, May 11.

Southwest flies direct from Oakland to Chicago.

There are 12 Southwest direct flights from Oakland to Chicago 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 Oakland to Chicago on a daily basis.

The cheapest direct (nonstop) round-trip flights between Oakland and Chicago start at $335 from Thu, Jul 9 to Wed, Jul 15 with Southwest.

It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Oakland to Chicago, 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 Oakland and Chicago start at $993 from Sat, May 30 to Sat, Jun 6 with Alaska.

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

To book business class trips from Oakland to Chicago, 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 Oakland and Chicago starts at $482 from Sat, May 9 to Mon, May 11 with Alaska.

The cheapest last-minute deal between Oakland and Chicago at price $482 is offered by Alaska from Sat, May 9 to Mon, May 11.

To find last-minute flight deals from Oakland to Chicago, 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.