Cheap flights from Oakland to Chicago

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Easily compare round trip flights from Oakland 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 to Chicago by changing tabs
Quickest
Cheapest
Spirit Airlines
Spirit Airlines
04 Sep
OAK
1:13 pm
Oakland airport
7h 50m
1 Stop
11:03 pm
ORD
Chicago O'Hare Intl airport
Spirit Airlines
18 Sep
ORD
10:40 am
Chicago O'Hare Intl airport
6h 55m
1 Stop
3:35 pm
OAK
Oakland airport
156 USD
Spirit Airlines
Spirit Airlines
09 Sep
OAK
2:20 pm
Oakland airport
6h 43m
1 Stop
11:03 pm
ORD
Chicago O'Hare Intl airport
Spirit Airlines
12 Sep
ORD
2:40 am
Chicago O'Hare Intl airport
7h 45m
1 Stop
8:25 am
OAK
Oakland airport
156 USD
Spirit Airlines
Spirit Airlines
08 Sep
OAK
2:20 pm
Oakland airport
6h 43m
1 Stop
11:03 pm
ORD
Chicago O'Hare Intl airport
Spirit Airlines
11 Sep
ORD
10:40 am
Chicago O'Hare Intl airport
10h 14m
1 Stop
6:54 pm
OAK
Oakland airport
161 USD
Spirit Airlines
Spirit Airlines
16 Jul
OAK
3:50 am
Oakland airport
4h 14m
10:04 am
ORD
Chicago O'Hare Intl airport
Spirit Airlines
31 Jul
ORD
12:55 pm
Chicago O'Hare Intl airport
4h 35m
3:30 pm
OAK
Oakland airport
186 USD
Southwest
Southwest
20 Jul
OAK
9:35 am
Oakland airport
5h 50m
1 Stop
5:25 pm
MDW
Chicago Midway airport
Southwest
27 Jul
MDW
12:55 am
Chicago Midway airport
4h 20m
3:15 am
OAK
Oakland airport
440 USD
Spirit Airlines
Spirit Airlines
06 Sep
OAK
4:50 pm
Oakland airport
4h 00m
10:50 pm
ORD
Chicago O'Hare Intl airport
Spirit Airlines
10 Sep
ORD
2:40 am
Chicago O'Hare Intl airport
7h 42m
1 Stop
8:22 am
OAK
Oakland airport
195 USD

How to get the cheapest flight ticket from Oakland 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
CHEAPEST MONTH TO FLY
September
The cheapest time of year to fly to Chicago from Oakland is September. Most expensive is December
CHEAPEST DAY TO FLY
Saturday
The cheapest day of the week is typically Saturday. The most expensive is typically Sunday
CHEAPEST TIME TO FLY
in the evening
Oakland to Chicago flights are approximately 122% more expensive in the afternoon than in the evening
CHEAPEST AIRLINE
Frontier
Frontier, Spirit Airlines, and Alaska Airlines are the most popular carriers operating from Oakland to Chicago
CHEAPEST ROUTE
Oakland - Chicago O'Hare Intl
Fly from Oakland to Chicago O'Hare Intl for the best Oakland - Chicago flight prices
CHEAPEST TIME TO BOOK
60 days before
The cheapest time to buy a flight from Oakland to Chicago is approximately 60 days to departure
60
Days before departure
0

Flight information for Oakland to Chicago (CHI - OAK)

Find info about flight duration, direct flights, and airports for your flight from Oakland to Chicago
Fastest flight time
4h 0m
The fastest flight from Oakland to Chicago takes 4h 0m.
Direct flights
Every day
Direct flights go from Oakland to Chicago every day.
Airports in Chicago
3 airports
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

Alternative routes for Oakland to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
San Francisco to Chicago
Fastest flight time
3h 58m
Cheapest price
216 USD

Flights from Oakland to:

  • Chicago
  • Illinois
  • United States
  • North America

Flights to Chicago from:

  • Oakland
  • California
  • United States
  • North America