Most accurate provider | FlightHub 3 stars |
---|---|
Most trusted provider | FlightHub 3 stars |
Popular in | June |
Cheapest in | April |
Round-trip from | $235 (Mytrip) |
One-way from | $59 (Cheapflightsfares) |
Fly from
Fly to
Route
Depart
Return
Price
OaklandChicago
OAK - ORD
OAKORD
Oakland
Thu 12/5
11:24 am-5:30 am
2 stops16h 06m
Chicago O'Hare Intl
Sun 12/8
6:33 pm-4:51 pm
3 stops24h 18m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Sat 2/22
3:20 pm-11:10 pm
1 stop5h 50m
Chicago Midway
Sat 3/1
5:10 pm-8:00 pm
Nonstop4h 50m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Tue 1/7
5:35 am-5:47 pm
2 stops10h 12m
Chicago Midway
Fri 1/10
10:57 am-11:56 pm
2 stops14h 59m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Wed 12/4
3:00 pm-2:15 pm
3 stops21h 15m
Chicago O'Hare Intl
Fri 12/6
9:32 pm-2:40 pm
3 stops19h 08m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Sat 2/22
8:32 pm-1:04 pm
1 stop14h 32m
Chicago O'Hare Intl
Sat 3/1
7:45 am-7:52 pm
1 stop14h 07m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Tue 12/17
12:55 pm-10:03 pm
1 stop7h 08m
Chicago O'Hare Intl
Thu 12/19
7:05 pm-12:20 am
1 stop7h 15m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Mon 1/13
6:32 am-12:13 am
2 stops15h 41m
Chicago Midway
Sun 1/19
7:15 am-10:39 pm
2 stops17h 24m
OaklandChicago
OAK - ORD
OAKORD
Oakland
Sat 3/15
5:15 am-4:25 pm
1 stop9h 10m
Chicago O'Hare Intl
Tue 3/18
6:00 am-11:00 am
1 stop7h 00m
OaklandChicago
OAK - MDW
OAKMDW
Oakland
Mon 3/17
11:59 pm-7:14 pm
1 stop17h 15m
Chicago Midway
Wed 3/19
8:39 pm-3:25 pm
2 stops20h 46m
OaklandChicago
OAK - RFD
OAKRFD
Oakland
Sat 12/21
6:36 pm-11:50 am
1 stop15h 14m
Chicago Greater Rockford
Sun 12/29
12:40 pm-8:30 pm
1 stop9h 50m
Provider | Price Accuracy | Trust Score* |
---|---|---|
Expedia | Price Accuracy1 star | Trust Score*3 stars |
FlightHub | Price Accuracy3 stars | Trust Score*3 stars |
eDreams | Price Accuracy3 stars | Trust Score*3 stars |
Priceline | Price Accuracy1 star | Trust Score*3 stars |
Cheapflightsfares | Price Accuracy3 stars | Trust Score*1 star |
CheapOair | Price Accuracy2 stars | Trust Score*3 stars |
The best time to book flights from Oakland, California to Chicago is 86 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Currently, September is the cheapest month in which you can book a flight from Oakland, California to Chicago (average of $232). Flying from Oakland, California to Chicago in June is currently the most expensive (average of $308). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
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 evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 25% on airfare.
Travelers seeking maximum savings on their Oakland, California to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Overall
Entertainment
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Boarding
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Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Overall
Entertainment
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Food
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Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Overall
Entertainment
Comfort
Food
Boarding
Crew
Reviews
My original flight was delayed so they found this flight for me so I could arrive at a reasonable time
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Frontier | Cheapest$72 | Average$242 | FlexibilityNo cancel fee | On-time62% |
Spirit Airlines | Cheapest$134 | Average$293 | FlexibilityNo cancel fee | On-time65% |
Alaska Airlines | Cheapest$138 | Average$416 | FlexibilityNo cancel fee | On-time75% |
Delta | Cheapest$236 | Average$467 | FlexibilityNo cancel fee | On-timeN/A |
Southwest | Cheapest$262 | Average$379 | FlexibilityNo cancel fee | On-time63% |