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Cheap flights from Oakland to Chicago (OAK - CHI)

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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)

OAK - CHI
Price
$223 - $326
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 inches
Popular in July High demand for flights, 18% potential price rise
Cheapest in October Best time to find cheap flights, 17% potential price drop
Round-trip from $223 From Oakland to Chicago
One-way from $46 One-way flight from Oakland to Chicago
Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Oakland to Chicago?

It’s generally more expensive to depart on a Monday, if you have to leave on this day you can still search on Cheapflights to find great options that meet your needs.

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

To save on the cost of your flight from Oakland to Chicago, book at least 37 days before your planned departure. Booking around this time can save you about 10% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $177 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $177.

Cheap flights from Oakland to Chicago in July, August 2020

The best prices found for OAK to CHI flights for July, August
14 Jul - 21 Jul
$86pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
8 Jul - 13 Jul
$88pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
29 Jul - 1 Aug
$90pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland

Oakland to Chicago 2020 flight deals

Cheap flights to Chicago from Oakland found for this year
14 Jul - 21 Jul
$86pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
8 Jul - 13 Jul
$88pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
29 Jul - 1 Aug
$90pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland

Non-stop flights to Chicago from Oakland

Save time with Oakland to Chicago direct flight deals
1 Jul - 8 Jul
$96pp
OAK
Oakland
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
OAK
Oakland
7 Jul - 23 Jul
$97pp
OAK
Oakland
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
OAK
Oakland
29 Jul - 3 Aug
$98pp
OAK
Oakland
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
OAK
Oakland

Last minute flights from Oakland to Chicago

Late deals on round-trip flights to Chicago from Oakland, departing today and this week
25 Jun - 27 Jul
$227pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
 
1 STOP
OAK
Oakland
25 Jun - 8 Jul
$228pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
OAK
Oakland
25 Jun - 2 Jul
$229pp
OAK
Oakland
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
OAK
Oakland

One-way flights to Chicago from Oakland

The cheapest one-way flights from Oakland to Chicago
12:14 pm - 6:21 pm
Spirit Airlines
Nonstop
4h 07m
OAK - ORD
Spirit Airlines
$46
KAYAK
12:14 pm - 6:21 pm
Spirit Airlines
Nonstop
4h 07m
OAK - ORD
Spirit Airlines
$47
KAYAK
12:14 pm - 6:21 pm
Spirit Airlines
Nonstop
4h 07m
OAK - ORD
Spirit Airlines
$49
FlightNetwork

Related info for your journey

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

Flight FAQs

From Oakland to Chicago

Are flight prices decreasing from Oakland to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Oakland and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Can I find flights from Oakland to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Oakland to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $86, but on average you can expect to pay $98.

Are there nonstop flights from Oakland to Chicago for under $100 on Cheapflights?

Cheapflights has at least 20 direct flights from Oakland to Chicago under $100. A good price for a nonstop flight from Oakland to Chicago is less than $105.

Are there last-minute flights available from Oakland to Chicago for under $300?

There are currently 20+ open flights from Oakland to Chicago within the next 7 days for less than $300.

What days are nonstop flights available from Oakland to Chicago?

Nonstop flights are available for this route on the following days: Friday, Saturday.

How popular is this flight route?

This flight path from Oakland to Chicago was viewed by 222 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

What is the cheapest airline for this route?

Southwest Airlines Co. offers the cheapest flights from Oakland to Chicago. Per day you can find on average 316 flights for this route and airline.

Is Oakland weather warmer or cooler than Chicago?

With an average temperature of 84 °F, peak weather can be found in July. As a traveler, expect to see changes in flight prices during that period. The temperatures in Chicago are hotter than in Oakland.

Alternative routes for Oakland to Chicago

Destination information for Chicago

Things to know before you go. Useful info for your trip from Oakland to Chicago
Flight duration
4h 18m
Average temperature for July in Chicago
84.2 °F
Avg rainfall for July in Chicago
3.7 ″

Airports servicing Oakland

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Hourly flight availability from Oakland to Chicago

Morning 6 AM to noon 59% of OAK to CHI departures
Afternoon Noon to 6 PM 40% of OAK to CHI departures
Early morning Midnight to 6 AM 1% of OAK to CHI departures
Evening 6 PM to midnight 0% of OAK to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Oakland to Chicago
Sunday
8 daily flights
Monday
8 daily flights
Tuesday
7 daily flights
Wednesday
7 daily flights
Thursday
8 daily flights
Friday
8 daily flights
Saturday
5 daily flights
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