Flights North America United States Illinois Chicago Oakland, California to Chicago

Cheap flights from Oakland, California to Chicago

Round-trip
Economy
San Francisco (SFO)
Chicago (CHI)
Fri 8/27
Fri 9/3
Any month
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Travel Restriction Alert

The COVID-19 (coronavirus) outbreak may impact travel from Oakland to Chicago.
View current United States travel restrictions

Flight information for Oakland, California to Chicago
(OAK to CHI)

Find info about flight duration, direct flights, and airports for your flight from Oakland, California to Chicago
Best Price Found$74The best flight deal from Oakland, California to Chicago found on momondo in the last 72 hours is $74
Fastest flight time4h 5mThe fastest flight from Oakland, California to Chicago takes 4h 5m
Direct flightsSuDirect flights go from Oakland, California to Chicago on Sunday. The only airline offering direct flights is Southwest.
Airports in Chicago3 airportsThere are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

How to get the cheapest flight ticket from Oakland, California to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

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

August
The cheapest time of year to fly to Chicago from Oakland, California is August. Most expensive is December

What is the cheapest day to depart Oakland, California for Chicago?

Tuesday
The cheapest day of the week is typically Tuesday. The most expensive is typically Sunday

When is the cheapest time to fly from Oakland, California to Chicago?

in the evening
Oakland, California to Chicago flights are approximately 18% more expensive at noon than in the evening

What is the cheapest airline that flies to Chicago from Oakland, California?

Frontier
Frontier, Alaska Airlines, and Spirit Airlines are the most popular carriers operating from Oakland, California to Chicago

What is the cheapest Oakland, California to Chicago flight route?

Oakland - Chicago O'Hare Intl
Fly from Oakland to Chicago O'Hare Intl for the best Oakland, California - Chicago flight prices

How far in advance should you book Oakland, California to Chicago flights?

53 days before
The cheapest time to buy a flight from Oakland, California to Chicago is approximately 53 days to departure
60
Days before departure
0

Easily compare round-trip flights from Oakland, California to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Oakland, California to Chicago by changing tabs
Spirit Airlines
Aug 26
OAK7:20 pmOakland
4h 05m
ORD11:25 pmChicago O'Hare Intl
Aug 31
ORD4:50 amChicago O'Hare Intl
5h 58m
1 stop
OAK10:48 amOakland
Spirit Airlines
Aug 26
OAK2:57 pmOakland
7h 37m
1 stop
ORD10:34 pmChicago O'Hare Intl
Aug 31
ORD3:45 pmChicago O'Hare Intl
4h 38m
OAK8:23 pmOakland
Spirit Airlines
Aug 26
OAK2:57 pmOakland
7h 37m
1 stop
ORD10:34 pmChicago O'Hare Intl
Sep 8
ORD1:26 pmChicago O'Hare Intl
6h 01m
1 stop
OAK7:27 pmOakland

Find the cheapest one-way flights from Oakland, California to Chicago

If you're looking for one-way flights from Oakland, California to Chicago, view some of our deals below provided by Spirit Airlines
Spirit Airlines
Aug 29
OAK7:20 pmOakland
4h 05m
ORD11:25 pmChicago O'Hare Intl
Spirit Airlines
Aug 26
OAK7:20 pmOakland
4h 05m
ORD11:25 pmChicago O'Hare Intl
Spirit Airlines
Aug 26
OAK4:26 amOakland
7h 35m
1 stop
ORD12:01 pmChicago O'Hare Intl

Best airlines flying from Oakland, California to Chicago

Compare and see reviews for airlines that fly from Oakland, California to Chicago with momondo
AirlineRatingFree CancellationPrice
Alaska Airlines
PriceFrom $123
Free Cancellation
Rating
8.3
8.7

Boarding

8.4

Comfort

8.7

Crew

8.1

Entertainment

7.6

Food

Reviews

Pros: The comfort of the plane was great! Lots of room and very comfortable seating.

Cons: I found some members of staff to be a bit rude. When other passengers asked questions or did something wrong (that was a minor issue), one of the staff members in particular talked down to them and treated them like they were stupid.

1 / 10
American Airlines
PriceFrom $138
Free Cancellation
Rating
7.2
7.4

Boarding

7.1

Comfort

7.8

Crew

7.0

Entertainment

6.8

Food

Reviews

Pros: Delayed flight no reasons seems like American Airlines don’t know what to do in these situations

Cons: I believe this airlines should have figured the answer to this question by now.

1 / 10
United Airlines
PriceFrom $138
Free Cancellation
Rating
6.8
7.2

Boarding

6.6

Comfort

7.5

Crew

6.6

Entertainment

6.1

Food

Reviews

Cons: Sarasota ticketing agent was not very nice at all 😟 Houston Gate agent was not nice either. We were treated like we were stupid for asking questions. I hope it’s not racism issues. I wished I had taken their names.

1 / 10
Spirit Airlines
PriceFrom $143
Free Cancellation
Rating
6.5
6.8

Boarding

6.2

Comfort

7.2

Crew

5.6

Entertainment

5.7

Food

Reviews

Pros: Well, it was not very comfortable and we were delayed for an hour. And a crew member was sick.

Cons: Mostly everything.

1 / 10
Delta
PriceFrom $147
Free Cancellation
Rating
8.2
8.3

Boarding

8.5

Comfort

8.3

Crew

7.9

Entertainment

8.0

Food

Reviews

Cons: Wouldn't let us on the flight when there was plenty of time to get there. Manager was arrogant and slow - didn't care. Poor policies at that airport.

1 / 10

Are airlines flying from Oakland to Chicago offering flexible cancellation due to COVID-19?

Some of our partner airlines flying from Oakland to Chicago are adopting new policies due to the global impact of COVID-19. Some of the airlines that may be waiving their cancellation fees are Spirit Airlines, United Airlines, and Delta. You can search for the full list of airlines like Spirit Airlines that are offering this flexibility.

How far is Oakland to Chicago by plane?

The distance between Oakland and Chicago is about 1845.3 mi. Typically, this will take 4h 05m by plane in normal conditions.

Can I fly to Chicago from Oakland right now?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from Oakland need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Oakland must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Oakland are not required to quarantine after entering Chicago.

Can I fly back to Oakland from Chicago?

Returning to Oakland from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Oakland.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Oakland.

If you are planning to travel to Chicago at this time, it is recommended that you stay up to date on current restrictions and follow proper safety measures while in public.
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