Cheap flights from Oakland (OAK) to Chicago (CHI)
The best prices from Oakland to Chicago are usually found in February or October, booked 16 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday
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 2023: compare Oakland to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
OAK - CHI Price | $213 - $441 |
|---|---|
CHI Temperature | 23 - 73.4 °F |
CHI Rainfall | 1.7 - 4.9 inches |
| Popular in | June | High demand for flights, 22% potential price rise |
|---|---|---|
| Cheapest in | February | Best time to find cheap flights, 38% potential price drop |
| Round-trip from | $213 | From Oakland to Chicago (CHI) |
| One-way from | $78 | One-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 35% by booking at least 24 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 $489.
What is the cheapest month to fly from Oakland, California to Chicago?
The best pricing can be found in the month of February. Prices to Chicago from Oakland, California average $437. You can even find prices in February for less than $437, as users have found deals to Chicago from as low as $197. 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 34%.
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 at noon tend to be the most expensive. A flight in the evening could potentially save you up to 30% on airfare.
Cheap flights from Oakland to Chicago in January, February 2023
The best prices found for OAK to CHI flights for January, February
Oakland
Chicago O'Hare Intl
1 stop
12h 59mChicago O'Hare Intl
Oakland
1 stop
8h 31mSpirit Airlines
Oakland
Chicago O'Hare Intl
1 stop
12h 59mChicago O'Hare Intl
Oakland
1 stop
10h 25mSpirit Airlines
Oakland
Chicago O'Hare Intl
1 stop
14h 23mChicago O'Hare Intl
Oakland
1 stop
8h 43mSpirit Airlines
Oakland to Chicago 2023 flight deals
Cheap flights to Chicago from Oakland found for this year
Oakland
Chicago O'Hare Intl
1 stop
10h 58mChicago O'Hare Intl
Oakland
1 stop
15h 16mSpirit Airlines
Oakland
Chicago O'Hare Intl
1 stop
12h 59mChicago O'Hare Intl
Oakland
1 stop
10h 25mSpirit Airlines
Oakland
Chicago O'Hare Intl
1 stop
14h 23mChicago O'Hare Intl
Oakland
1 stop
8h 43mSpirit Airlines
Cheap Spirit Airlines flights from Oakland to Chicago
Oakland
Chicago O'Hare Intl
1 stop
12h 59mChicago O'Hare Intl
Oakland
1 stop
8h 31mSpirit Airlines
Oakland
Chicago O'Hare Intl
1 stop
12h 59mChicago O'Hare Intl
Oakland
1 stop
10h 25mSpirit Airlines
Oakland
Chicago O'Hare Intl
1 stop
14h 23mChicago O'Hare Intl
Oakland
1 stop
8h 43mSpirit Airlines
Cheap Frontier flights from Oakland to Chicago
Oakland
Chicago Midway
1 stop
13h 21mChicago Midway
Oakland
1 stop
23h 53mFrontier
Oakland
Chicago Midway
1 stop
10h 40mChicago Midway
Oakland
1 stop
21h 22mFrontier
Oakland
Chicago Midway
1 stop
15h 30mChicago Midway
Oakland
1 stop
21h 22mFrontier
Non-stop flights to Chicago from Oakland
Save time with Oakland to Chicago direct flight deals
Oakland
Chicago O'Hare Intl
Nonstop
4h 00mChicago O'Hare Intl
Oakland
Nonstop
4h 35mSpirit Airlines
Oakland
Chicago O'Hare Intl
Nonstop
4h 00mChicago O'Hare Intl
Oakland
Nonstop
4h 35mSpirit Airlines
Oakland
Chicago O'Hare Intl
Nonstop
4h 00mChicago O'Hare Intl
Oakland
Nonstop
4h 35mSpirit Airlines
Last minute flights from Oakland to Chicago
Late deals on return flights to Chicago from Oakland, departing today and this week
Oakland
Chicago O'Hare Intl
1 stop
12h 59mChicago O'Hare Intl
Oakland
1 stop
8h 31mSpirit Airlines
Oakland
Chicago O'Hare Intl
1 stop
12h 59mChicago O'Hare Intl
Oakland
1 stop
10h 25mSpirit Airlines
Oakland
Chicago O'Hare Intl
1 stop
8h 58mChicago O'Hare Intl
Oakland
1 stop
6h 21mSpirit Airlines
One-way flights to Chicago from Oakland
The cheapest one-way flights from Oakland to Chicago
Oakland
Chicago O'Hare Intl
1 stop
15h 54mMultiple Airlines
Oakland
Chicago O'Hare Intl
1 stop
14h 16mSpirit Airlines
Oakland
Chicago O'Hare Intl
1 stop
12h 59mSpirit Airlines
Reviews of Airlines Servicing Chicago
Crew
Comfort
Overall
Food
Boarding
Entertainment
Reviews
Short flight from DC to Nashville. No food ordered. Plane was not full at all. No one around me. Smooth flight. Polite staff. Arrived early.
Crew
Comfort
Overall
Food
Boarding
Entertainment
Reviews
Short flight from DC to Nashville. No food ordered. Plane was not full at all. No one around me. Smooth flight. Polite staff. Arrived early.
Crew
Comfort
Overall
Food
Boarding
Entertainment
Reviews
Short flight from DC to Nashville. No food ordered. Plane was not full at all. No one around me. Smooth flight. Polite staff. Arrived early.
Crew
Comfort
Overall
Food
Boarding
Entertainment
Reviews
Short flight from DC to Nashville. No food ordered. Plane was not full at all. No one around me. Smooth flight. Polite staff. Arrived early.
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 3 daily outbound flights to Chicago from 8 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, United Airlines, and Delta 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 $108, but on average you can expect to pay $122.
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 $328.
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 $108. Another airline that can offer you cheap pricing is Frontier. Users have found that Spirit Airlines is 68% 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 $175, our data shows the cheapest flight currently is $76. When looking at the most popular route, (Oakland - Chicago O'Hare Intl), you can expect to pay $110 for that flight.
Other flights from Oakland
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.
Hourly flight availability from Oakland to Chicago
See what time of day planes typically take off from Oakland to Chicago
| 25%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 25%of flight departures | Morning6 am to noon |
| 50%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |
Weekly flight availability from Oakland to Chicago
See how many times per day planes take to the skies headed from Oakland to Chicago
| Sunday | 1daily flight |
|---|---|
| Monday | 4daily flights |
| Tuesday | 4daily flights |
| Wednesday | 4daily flights |
| Thursday | 4daily flights |
| Friday | 4daily flights |
| Saturday | 1daily flight |