Cheap flights from Oakland, California to Chicago from $96

Round-trip
1 adult
Economy
From?
To?
Sun 6/11
Sun 6/18

Deals available from 900+ travel sites.

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

$96

Fastest flight time

4h 00m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Oakland, California in the past 72 hours is $96. The best round-trip flight deal from Oakland, California to Chicago found on momondo in the last 72 hours is $207.
The fastest flight from Oakland, California to Chicago takes 4h 00m
Direct flights go from Oakland, California to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

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?

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

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

Wednesday. The cheapest day of the week is typically Wednesday. The most expensive is typically Saturday

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

In the evening. Oakland, California to Chicago flights are approximately 26% more expensive in the afternoon than in the evening

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

Frontier. Alaska Airlines, American Airlines, and Delta 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?

15 days before. The cheapest time to buy a flight from Oakland, California to Chicago is approximately 15 days to departure

How many flights depart from Oakland, California to Chicago on average per day?

7 flights are operational weekly from Oakland, California to Chicago as of June 2023. The most popular departure time for this route is 4:00AM, with 50% of flights per day taking off at noon.

How many flights depart from Oakland, California to Chicago on average per week?

As of June 2023, 52 flights take off from Oakland, California and land in Chicago each week. The most common flight departure day for this route is Monday, with 19% of weekly flights taking off on this day.

Can stopping save me money on Oakland, California to Chicago flights?

You could potentially save up to 13% on your flight if you consider stops on a Oakland, California to Chicago flight.

If you are looking to fly from Oakland to Chicago, you are most likely going to fly from Oakland Airport to Chicago O'Hare Intl Airport, the most popular airports on that route. You may be looking for an airport near Oakland Airport to depart from when traveling to Chicago and luckily, there are options! You can try San Francisco Airport which is located in San Francisco, San Jose Airport which is located in San Jose, or Santa Rosa Sonoma County Airport which is located in Santa Rosa. You may be looking for an airport near Chicago O'Hare Intl Airport to land at when traveling from Oakland and luckily, there are options! You can try Chicago Midway Airport which is located in Chicago or Chicago Greater Rockford Airport which is located in Chicago. The cheapest route from Oakland to Chicago is OAK — ORD with an average price of $150 RT during the month of June.

San Francisco Airport (SFO) to Chicago O'Hare Intl Airport (ORD)$218
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San Francisco Airport (SFO) to Chicago Midway Airport (MDW)$199
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Oakland Airport (OAK) to Chicago O'Hare Intl Airport (ORD)$150
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San Jose Airport (SJC) to Chicago O'Hare Intl Airport (ORD)$217
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San Jose Airport (SJC) to Chicago Midway Airport (MDW)$243
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Oakland Airport (OAK) to Chicago Midway Airport (MDW)$246
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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 six 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 22
OAK9:46 amOakland
8h 10m
1 stop
ORD5:56 pmChicago O'Hare Intl
Aug 29
ORD7:35 pmChicago O'Hare Intl
15h 14m
1 stop
OAK10:49 amOakland
Multiple Airlines
Aug 22
OAK9:46 amOakland
28h 52m
2 stops
MDW2:38 pmChicago Midway
Aug 29
MDW5:09 pmChicago Midway
27h 45m
2 stops
OAK8:54 pmOakland
Spirit Airlines
Aug 28
OAK4:05 pmOakland
14h 31m
1 stop
ORD6:36 amChicago O'Hare Intl
Aug 29
ORD7:35 pmChicago O'Hare Intl
15h 14m
1 stop
OAK10:49 amOakland
Spirit Airlines
Jul 10
OAK5:20 pmOakland
13h 08m
1 stop
ORD6:28 amChicago O'Hare Intl
Jul 12
ORD7:35 pmChicago O'Hare Intl
15h 15m
1 stop
OAK10:50 amOakland
Multiple Airlines
Jun 21
OAK4:50 pmOakland
13h 37m
1 stop
MDW6:27 amChicago Midway
Jun 27
MDW2:16 pmChicago Midway
6h 38m
1 stop
OAK8:54 pmOakland
Multiple Airlines
Jun 27
OAK4:50 pmOakland
13h 52m
1 stop
MDW6:42 amChicago Midway
Jul 5
MDW1:52 pmChicago Midway
20h 58m
1 stop
OAK10:50 amOakland

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 Southwest and Spirit Airlines
Multiple Airlines
Aug 23
OAK1:45 amOakland
12h 53m
2 stops
MDW2:38 pmChicago Midway
Spirit Airlines
Jun 21
OAK9:46 amOakland
8h 34m
1 stop
ORD6:20 pmChicago O'Hare Intl
Southwest
Oct 3
OAK2:05 pmOakland
4h 05m
MDW6:10 pmChicago Midway

Search last-minute flights to Chicago from Oakland, California

Find and compare round-trip flight prices for your last-minute flight from Oakland, California to Chicago
Spirit Airlines
Jun 15
OAK3:56 pmOakland
14h 36m
1 stop
ORD6:32 amChicago O'Hare Intl
Jun 21
ORD6:30 pmChicago O'Hare Intl
16h 20m
1 stop
OAK10:50 amOakland
Multiple Airlines
Jun 12
OAK3:56 pmOakland
15h 27m
1 stop
MDW7:23 amChicago Midway
Jun 20
MDW4:30 pmChicago Midway
42h 20m
2 stops
OAK10:50 amOakland
Spirit Airlines
Jun 12
OAK3:56 pmOakland
21h 23m
2 stops
ORD1:19 pmChicago O'Hare Intl
Jun 20
ORD6:30 pmChicago O'Hare Intl
16h 20m
1 stop
OAK10:50 amOakland
Multiple Airlines
Jun 12
OAK3:56 pmOakland
15h 27m
1 stop
MDW7:23 amChicago Midway
Jun 21
MDW9:18 amChicago Midway
25h 32m
2 stops
OAK10:50 amOakland
Multiple Airlines
Jun 12
OAK3:56 pmOakland
15h 27m
1 stop
MDW7:23 amChicago Midway
Jun 27
MDW3:38 pmChicago Midway
25h 28m
1 stop
OAK5:06 pmOakland
Spirit Airlines
Jun 12
OAK2:47 pmOakland
12h 00m
1 stop
ORD2:47 amChicago O'Hare Intl
Jul 12
ORD7:35 pmChicago O'Hare Intl
15h 15m
1 stop
OAK10:50 amOakland

Best airlines flying from Oakland, California to Chicago

Compare and see reviews for airlines that fly from Oakland, California to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Alaska AirlinesPriceFrom $142Free CancellationRating
7.9
2,038 reviews
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United AirlinesPriceFrom $149Free CancellationRating
7.2
2,131 reviews
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FrontierPriceFrom $164Free CancellationRating
6.1
847 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $166Free CancellationRating
6.1
2,210 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $183Free CancellationRating
7.2
2,311 reviews
Search American Airlines flights
DeltaPriceFrom $245Free CancellationRating
7.8
1,279 reviews
Search Delta flights

Spirit Airlines flights from Oakland, California to Chicago

Our best Spirit Airlines deals on Oakland, California to Chicago flight tickets
Spirit Airlines
Aug 22
OAK9:46 amOakland
8h 10m
1 stop
ORD5:56 pmChicago O'Hare Intl
Aug 29
ORD7:35 pmChicago O'Hare Intl
15h 14m
1 stop
OAK10:49 amOakland
Spirit Airlines
Aug 28
OAK4:05 pmOakland
14h 31m
1 stop
ORD6:36 amChicago O'Hare Intl
Aug 29
ORD7:35 pmChicago O'Hare Intl
15h 14m
1 stop
OAK10:49 amOakland
Spirit Airlines
Jul 10
OAK5:20 pmOakland
13h 08m
1 stop
ORD6:28 amChicago O'Hare Intl
Jul 12
ORD7:35 pmChicago O'Hare Intl
15h 15m
1 stop
OAK10:50 amOakland

  • How far is Oakland to Chicago by plane?

    The distance between Oakland and Chicago is about 1845.3 mi. Typically, this will take 8h 10m by plane in normal conditions.


Alternative routes for Oakland, California to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Los Angeles to Chicago Flights
Fastest flight time3h 52m
Cheapest price$159
San Francisco to Chicago Flights
Fastest flight time4h 03m
Cheapest price$199
Burbank to Chicago Flights
Fastest flight time6h 11m
Cheapest price$225
San Diego to Chicago Flights
Fastest flight time3h 55m
Cheapest price$187
Ontario to Chicago Flights
Fastest flight time5h 40m
Cheapest price$197
San Jose to Chicago Flights
Fastest flight time4h 17m
Cheapest price$231
Sacramento to Chicago Flights
Fastest flight time3h 58m
Cheapest price$241
Los Angeles to St. Louis Flights
Fastest flight time3h 34m
Cheapest price$146
Santa Ana to Chicago Flights
Fastest flight time7h 26m
Cheapest price$182
Long Beach to Chicago Flights
Fastest flight time5h 37m
Cheapest price$257
San Francisco to St. Louis Flights
Fastest flight time5h 55m
Cheapest price$150
Ontario to St. Louis Flights
Fastest flight time4h 58m
Cheapest price$175

Why use momondo?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Oakland.

momondo does allow users to show only those flights to Chicago from Oakland which offer a flexible booking policy as well as other useful filters and features.


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