Cheap flights from Oakland, CA to Chicago, IL

Flights starting at £59. Choose between Spirit Airlines, Delta Air Lines, or Frontier Airlines to find the best price.

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Tips to know when travelling to Chicago

One-way trips

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Round trips

Oakland OAKLos Angeles LAXLas Vegas LASOakland OAK

Spirit Airlines

£135
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Multiple carriers

£125

Updated:

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Travelers usually depart from Oakland International, Oakland, Emeryville, CA station, Oakland Jack London Square, or West Oakland Station when they travel from Oakland to Chicago. Book your trip to arrive at O Hare International, Chicago Midway International, Chicago, IL - Union Station, Chicago Rockford International, or Chicago Downtown Greyhound Station. The most popular airlines for this route are Spirit Airlines, Delta Air Lines, Frontier Airlines, United Airlines, and Allegiant Air. Oakland and Chicago have 401 direct flights per week.

Check-in for a flight from Oakland to Chicago

NameCarrier codeIATA CodePassport needed during bookingOnline check-in available
Spirit AirlinesNKSNKNoOpens 24 days before flight
Closes 1 hours before flight
Delta Air LinesDALDLYesOpens 24 days before flight
Closes 1 hours before flight
Frontier AirlinesFFTF9NoOpens 24 days before flight
Closes 1 hours before flight
United AirlinesUALUAYesNo
Allegiant AirAAYG4NoOpens 24 days before flight
Closes 1 hours before flight

Chicago travel tips

1) Experience the sense of humour of Chicagoans at the Second City Chicago Comedy Theater

The downtown is home to Second City Chicago, one of the most popular comedy theatres on the planet. Many famous comedians have visited its stage, and some of them later became cult figures in this business. Bill Murray, John Belushi, Stephen Colbert, and others are among them. Today comedians perform on two stages, "Mainstage Second City" and "The Second City". Check out the schedule for a fun evening.

2) See what the famous house near Chicago from the Home Alone movie looks like now

The famous house from the Home Alone movie is located in the town of Winnetka, 26 kilometres from downtown Chicago. Inside, this house has changed a lot in 30 years, but you can come here and take a souvenir photo if you are a movie fan.

3) Explore the Field Museum of Natural History in Chicago

This museum was built in neoclassical style in Chicago for the World’s Columbian Exposition in 1893. The museum now hosts over 24 million objects, many interesting exhibits on mummies, dinosaur fossils, precious gemstones, meteorites, and much more. Also, there is a library with 275,000+ books. The ticket costs $40.

United States COVID-19 travel restrictions

Your trip summary

Most travelers from Oakland, OAK can enter Chicago, ORD.

Departure

Additional information
  • Masks are recommended in certain settings

Return

Travel restrictions
  • Travel is allowed
  • Proof of a negative pre-departure COVID-19 test result is not required
  • Quarantine is not required

Information is provided as guidance only and accurate at the time of publishing. Always check government websites and airline materials before booking and traveling.

Learn more about COVID-19 restrictions in United States in our dedicated Stories article.

Frequently asked questions

What are the most popular routes to and from Oakland?
Travelers frequently search for route combinations, such as Oakland and Los Angeles, Las Vegas, Vilnius, London, Dublin, Bellingham, Mexico City, Kyiv, Kahului, Manchester, Cincinnati, Long Beach, New York, Rome, Edinburgh, Phoenix, Athens, Barcelona, Amsterdam, Charlotte.
What are the most popular routes to and from Chicago?
Travelers frequently search for route combinations, such as Chicago and London, Dublin, Manchester, Toronto, Athens, Orlando, San Francisco, Hyderabad, Vilnius, New York, Las Vegas, Edinburgh, Denver, Bangkok, Minneapolis, Riga, Glasgow, Austin, San Juan, Edmonton.
What airports are near Oakland?
The main airport in Oakland is Oakland International. It is also served by San Francisco International, Sacramento International, Oakland International, San Jose International, Stockton Metropolitan, Monterey Regional, Charles M. Schulz–Sonoma County, Merced Regional, Buchanan Field.
What airports are near Chicago?
The main airport in Chicago is O Hare International. It is also served by Gerald R. Ford International, General Mitchell International, Dane County Regional, General Wayne A. Downing Peoria International, Fort Wayne International, Central Illinois Regional, Quad City International, South Bend International, Muskegon County, Kalamazoo/Battle Creek International.
What buses and trains depart from Oakland?
A number of bus and train companies depart from Oakland, including Greyhound.
Is it possible to combine flights, buses, and trains in one itinerary when traveling between Oakland and Chicago?
Yes, it's possible to combine different modes of transport between Oakland and Chicago thanks to our Virtual Interlining technology. Making use of not only flights but also trains and buses between Oakland and Chicago can give rise to new adventures. Read more about how Virtual Interlining works on Kiwi.com Stories.
What is Virtual Interlining and how do I use it?
Virtual Interlining provides a revolutionary way of traveling. You can combine different modes of transport like flights, trains, and buses into one itinerary. And this often saves money. Thanks to the world's largest carrier database, the Kiwi.com search function enables anyone to mix and match different modes of transport easily.
Which airlines fly between Oakland and Chicago?
Currently, you can fly between Oakland and Chicago with Spirit Airlines, Delta Air Lines, Frontier Airlines, United Airlines, Allegiant Air.
When's the best time to travel between Oakland and Chicago?
If you don’t have specific dates for your trip between Oakland and Chicago, you can enter a date range into the departure and return fields. Most carriers on the Kiwi.com website allow you to search and book up to six months from the day of your search. Order the search results by the best, cheapest, or fastest route, or find the cheapest outbound and return combination in the pricing table.
What flights operate between Oakland and Chicago?
How many airports are there near Oakland?
How many airports are there near Chicago?
Is it possible to reach Oakland by bus or train?
What time do nonstop (direct) flights between Oakland and Chicago depart?
What time do nonstop (direct) flights between Oakland and Chicago arrive?
What time do flights between Oakland and Chicago depart?
What time do flights between Oakland and Chicago arrive?

Planning a trip? Thanks to our Virtual Interlining algorithm, we offer billions of route combinations between any A and any B in the world by plane, train, and bus. Find the cheapest routes and best deals for you, as well as the best dates on which to travel.

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