Cheap flights from Oakland (OAK) to Chicago (CHI)

OAK — CHI
Aug 15 — Aug 221

The best prices from Oakland to Chicago are usually found in October or September, booked 60 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

How to find the cheapest flight from Oakland (OAK) to Chicago (CHI)

All the information you need to plan the best OAK to CHI flight in 2022: compare Oakland to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.

OAK - CHI

Price

$164 - $441

CHI

Temperature

23 - 73.4 °F

CHI

Rainfall

1.7 - 4.9 inches

Popular inJuneHigh demand for flights, 29% potential price rise
Cheapest inOctoberBest time to find cheap flights, 48% potential price drop
Round-trip from$164From Oakland to Chicago (CHI)
One-way from$101One-way flight from Oakland to Chicago (CHI)

What is the cheapest day to fly round-trip from Oakland, California to Chicago?

Flying to your destination on a Saturday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Chicago. Check prices with Cheapflights to find a great deal for your trip.

How far in advance should I book a flight from Oakland, California to Chicago?

Find a great deal and save up to 54% by booking at least 61 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Oakland, California to Chicago within the next two weeks, with the cheapest ticket starting at $454.

What is the cheapest month to fly from Oakland, California to Chicago?

The best pricing can be found in the month of October. Prices to Chicago from Oakland, California average $384. You can even find prices in October for less than $384, as users have found deals to Chicago from as low as $157. The month of June appears to be one of the more expensive times to travel to Chicago from Oakland, California. Flying in the targeted month can save you up to 52%.

When is the cheapest time to fly from Oakland, California to Chicago (OAK - CHI)?

One of the essential ways to save on airfare from Oakland, California to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 22% on airfare.

Cheap flights from Oakland to Chicago in August, September 2022

The best prices found for OAK to CHI flights for August, September
Sep 16 - Sep 17
OAK

Oakland

ORD

Chicago O'Hare Intl

1 stop

5h 40m
ORD

Chicago O'Hare Intl

OAK

Oakland

1 stop

9h 30m
$148

Spirit Airlines

Pick Dates

Deal found 8/7/22

Sep 3 - Sep 14
OAK

Oakland

ORD

Chicago O'Hare Intl

1 stop

10h 47m
ORD

Chicago O'Hare Intl

OAK

Oakland

1 stop

10h 20m
$153

Spirit Airlines

Pick Dates

Deal found 8/9/22

Sep 28 - Oct 3
OAK

Oakland

MDW

Chicago Midway

1 stop

12h 21m
MDW

Chicago Midway

OAK

Oakland

1 stop

16h 30m
$161

Frontier

Pick Dates

Deal found 8/7/22

Oakland to Chicago 2022 flight deals

Cheap flights to Chicago from Oakland found for this year
Sep 16 - Sep 17
OAK

Oakland

ORD

Chicago O'Hare Intl

1 stop

5h 40m
ORD

Chicago O'Hare Intl

OAK

Oakland

1 stop

9h 30m
$148

Spirit Airlines

Pick Dates

Deal found 8/7/22

Sep 3 - Sep 14
OAK

Oakland

ORD

Chicago O'Hare Intl

1 stop

10h 47m
ORD

Chicago O'Hare Intl

OAK

Oakland

1 stop

10h 20m
$153

Spirit Airlines

Pick Dates

Deal found 8/9/22

Sep 28 - Oct 3
OAK

Oakland

MDW

Chicago Midway

1 stop

12h 21m
MDW

Chicago Midway

OAK

Oakland

1 stop

16h 30m
$161

Frontier

Pick Dates

Deal found 8/7/22

Cheap Spirit Airlines flights from Oakland to Chicago

Sep 16 - Sep 17
OAK

Oakland

ORD

Chicago O'Hare Intl

1 stop

5h 40m
ORD

Chicago O'Hare Intl

OAK

Oakland

1 stop

9h 30m
$148

Spirit Airlines

Pick Dates

Deal found 8/7/22

Sep 3 - Sep 14
OAK

Oakland

ORD

Chicago O'Hare Intl

1 stop

10h 47m
ORD

Chicago O'Hare Intl

OAK

Oakland

1 stop

10h 20m
$153

Spirit Airlines

Pick Dates

Deal found 8/9/22

Aug 23 - Aug 23
OAK

Oakland

ORD

Chicago O'Hare Intl

1 stop

9h 20m
ORD

Chicago O'Hare Intl

OAK

Oakland

Nonstop

4h 37m
$163

Spirit Airlines

Pick Dates

Deal found 8/8/22

Cheap Frontier flights from Oakland to Chicago

Sep 28 - Oct 3
OAK

Oakland

MDW

Chicago Midway

1 stop

12h 21m
MDW

Chicago Midway

OAK

Oakland

1 stop

16h 30m
$161

Frontier

Pick Dates

Deal found 8/7/22

Oct 5 - Oct 11
OAK

Oakland

MDW

Chicago Midway

1 stop

12h 15m
MDW

Chicago Midway

OAK

Oakland

1 stop

16h 15m
$162

Frontier

Pick Dates

Deal found 8/9/22

Oct 5 - Oct 11
OAK

Oakland

MDW

Chicago Midway

1 stop

12h 15m
MDW

Chicago Midway

OAK

Oakland

2 stops

25h 23m
$163

Frontier

Pick Dates

Deal found 8/9/22

Non-stop flights to Chicago from Oakland

Save time with Oakland to Chicago direct flight deals
Sep 4 - Sep 15
OAK

Oakland

ORD

Chicago O'Hare Intl

Nonstop

4h 10m
ORD

Chicago O'Hare Intl

OAK

Oakland

Nonstop

4h 48m
$166

Spirit Airlines

Pick Dates

Deal found 8/10/22

Aug 30 - Sep 6
OAK

Oakland

ORD

Chicago O'Hare Intl

Nonstop

4h 10m
ORD

Chicago O'Hare Intl

OAK

Oakland

Nonstop

4h 37m
$175

Spirit Airlines

Pick Dates

Deal found 8/10/22

Sep 4 - Sep 15
OAK

Oakland

ORD

Chicago O'Hare Intl

Nonstop

4h 10m
ORD

Chicago O'Hare Intl

OAK

Oakland

Nonstop

4h 48m
$178

Spirit Airlines

Pick Dates

Deal found 8/9/22

Last minute flights from Oakland to Chicago

Late deals on return flights to Chicago from Oakland, departing today and this week
Aug 15 - Aug 22
OAK

Oakland

MDW

Chicago Midway

1 stop

13h 18m
MDW

Chicago Midway

OAK

Oakland

1 stop

16h 29m
$164

Frontier

Pick Dates

Deal found 8/8/22

Aug 17 - Aug 22
OAK

Oakland

MDW

Chicago Midway

1 stop

13h 12m
MDW

Chicago Midway

OAK

Oakland

1 stop

16h 29m
$168

Frontier

Pick Dates

Deal found 8/10/22

Aug 19 - Aug 29
OAK

Oakland

MDW

Chicago Midway

2 stops

20h 32m
MDW

Chicago Midway

OAK

Oakland

1 stop

16h 29m
$169

Frontier

Pick Dates

Deal found 8/8/22

One-way flights to Chicago from Oakland

The cheapest one-way flights from Oakland to Chicago
Sep 24
OAK

Oakland

ORD

Chicago O'Hare Intl

1 stop

7h 48m
$79

Spirit Airlines

Pick Dates

Deal found 8/9/22

Sep 8
OAK

Oakland

ORD

Chicago O'Hare Intl

1 stop

9h 57m
$83

Spirit Airlines

Pick Dates

Deal found 8/8/22

Aug 17
OAK

Oakland

RFD

Chicago Greater Rockford

1 stop

12h 19m
$84

Multiple Airlines

Pick Dates

Deal found 8/7/22

Related info for your journey

Useful info, stats and facts about Oakland to Chicago flights.

What airport do you fly from for flights from Oakland to Chicago?

Located just 7.0 mi from the city center, Oakland is the airport most travelers will use when flying to Chicago from Oakland. Booking flights from Oakland (OAK) to Chicago should be relatively easy as there are 7 daily outbound flights to Chicago from 7 different airlines.

Which airlines flying from Oakland to Chicago have flexible cancellations due to COVID-19?

Some of our airline partners flying from Oakland to Chicago have new flexible policies in place due to COVID-19. Spirit Airlines, Delta, and United Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like Spirit Airlines with this kind of flexibility.

Can I find flights from Oakland, California to Chicago for under $200 on Cheapflights?

Yes, there are multiple flights from Oakland, California to Chicago for under $200. The cheapest flight booked recently is on Spirit Airlines for just $148, but on average you can expect to pay $166.

Are there nonstop flights from Oakland, California to Chicago for under $200 on Cheapflights?

Cheapflights has at least 20 direct flights from Oakland, California to Chicago under $200. A good price for a nonstop flight from Oakland, California to Chicago is less than $202.

Are there last-minute flights available from Oakland, California to Chicago for under $200?

There are currently 20+ open flights from Oakland, California to Chicago within the next 7 days for less than $200.

What are the cheapest airlines flying from Oakland, California to Chicago round-trip?

Cheapflights users have booked flights from Oakland, California to Chicago round-trip from $148. Another airline that can offer you cheap pricing is Frontier. Users have found that Spirit Airlines is 52% cheaper than the other options available to this destination.

What are the most popular routes from Oakland, California to Chicago?

The most popular flight routes from Oakland, California to Chicago are Oakland - Chicago O'Hare Intl, Oakland - Chicago Midway and Oakland - Chicago Greater Rockford.

What are the most popular airlines that fly from Oakland, California to Chicago?

American Airlines, Alaska Airlines and Delta are the most popular airlines when flying from Oakland, California to Chicago.

What are the cheapest flights from Oakland, California to Chicago?

While on average a flight from Oakland, California to Chicago is generally $390, our data shows the cheapest flight currently is $78. When looking at the most popular route, (Oakland - Chicago O'Hare Intl), you can expect to pay $163 for that flight.

Alternative routes for Oakland to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top 7 airlines flying from Oakland to Chicago

The chart below displays the airlines Cheapflights users traveling from Oakland to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
AirlineCheapestAverageFlexibilityOn-timeCOVID-19 safety
Juneyao AirlinesCheapest$14Average$24FlexibilityNo cancel feeOn-time66%COVID-19 safety
Search Juneyao Airlines flights
Alaska AirlinesCheapest$107Average$232FlexibilityNo cancel feeOn-time75%COVID-19 safety
Search Alaska Airlines flights
FrontierCheapest$111Average$346FlexibilityNo cancel feeOn-time62%COVID-19 safety
Search Frontier flights
Spirit AirlinesCheapest$117Average$339FlexibilityNo cancel feeOn-time65%COVID-19 safety
Search Spirit Airlines flights
United AirlinesCheapest$129Average$470FlexibilityNo cancel feeOn-time69%COVID-19 safety
Search United Airlines flights
American AirlinesCheapest$169Average$374FlexibilityNo cancel feeOn-time71%COVID-19 safety
Search American Airlines flights
DeltaCheapest$211Average$547FlexibilityNo cancel feeOn-timeN/ACOVID-19 safety
Search Delta flights

Hourly flight availability from Oakland to Chicago

See what time of day planes typically take off from Oakland to Chicago
24%of flight departuresEarly morningMidnight to 6 am
53%of flight departuresMorning6 am to noon
23%of flight departuresAfternoonNoon to 6 pm
0%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Oakland to Chicago

See how many times per day planes take to the skies headed from Oakland to Chicago
Sunday8daily flights
Monday8daily flights
Tuesday8daily flights
Wednesday8daily flights
Thursday8daily flights
Friday8daily flights
Saturday5daily flights