Cheap Flights from Santa Rosa to Chicago from $355

Compare Santa Rosa to Chicago flight deals

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Flight deals from Santa Rosa to Chicago

Looking for a cheap last-minute deal or the best return flight from Santa Rosa to Chicago? Find the lowest prices on one-way and return tickets right here.

Chicago.$522 per passenger.Departing Tue, 6 May, returning Sat, 10 May.Return flight with Alaska Airlines and Spirit Airlines.Outbound indirect flight with Alaska Airlines, departs from Santa Rosa on Tue, 6 May, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sat, 10 May, arriving in Santa Rosa.Price includes taxes and charges.From $522, select.

Chicago.$932 per passenger.Departing Thu, 7 Aug, returning Sun, 10 Aug.Return flight with Alaska Airlines and Spirit Airlines.Outbound indirect flight with Alaska Airlines, departs from Santa Rosa on Thu, 7 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Sun, 10 Aug, arriving in Santa Rosa.Price includes taxes and charges.From $932, select.

Chicago.$1,061 per passenger.Departing Sun, 20 Jul, returning Mon, 28 Jul.Return flight with Alaska Airlines and Spirit Airlines.Outbound indirect flight with Alaska Airlines, departs from Santa Rosa on Sun, 20 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with Spirit Airlines, departs from Chicago O'Hare International on Mon, 28 Jul, arriving in Santa Rosa.Price includes taxes and charges.From $1,061, select.

Find the cheapest month to fly from Santa Rosa to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Santa Rosa to Chicago flights are currently cheapest in May.

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Alternative Santa Rosa to Chicago routes

Looking for the cheapest, fastest or easiest route from Santa Rosa to Chicago? You could fly into the following airports instead.

Santa Rosa to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$522
Cheapest month to fly	May

Finding cheap flights from Santa Rosa to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are return flights from Santa Rosa to Chicago?

The best price we found for a return flight from Santa Rosa to Chicago is $522. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

Which airlines fly direct from Santa Rosa to Chicago?

Currently, there are no airlines that fly direct from Santa Rosa to Chicago. But we found flights with one or more stops from $522.

How many flights are there a week from Santa Rosa to Chicago?

As of April 2025, there are no flights flying from Santa Rosa to Chicago.

When is the cheapest time to fly from Santa Rosa to Chicago?

The cheapest month to fly from Santa Rosa to Chicago is usually May.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Santa Rosa Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $522.

Which upcoming date is cheapest to fly from Santa Rosa Airport to Chicago on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Santa Rosa Airport to Chicago on Tuesday, 6 May 2025.

Can I get a direct flight from Santa Rosa Airport to Chicago?

No airlines currently offer direct flights between Santa Rosa Airport and Chicago. Most routes have one or more stops.

How can I get the best flight deal from Santa Rosa Airport to Chicago?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

What’s the weather like in Chicago?

In April, the average temperature is usually around 8°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

Which is the cheapest airline to fly from Santa Rosa Airport to Chicago with?

Currently, Alaska Airlines offers the cheapest flight tickets to Chicago.

How to find cheap flights to Chicago from Santa Rosa

Looking for cheap tickets from Santa Rosa to Chicago? Here are a few tips on how to secure the best flight price and make your journey as smooth as possible.

Simply hit 'search'. From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Santa Rosa to Chicago. And with us there are no hidden fees - what you see is what you pay.
Compare flight deals to Chicago from Santa Rosa from over 1,000 providers. Then choose the cheapest or fastest plane tickets.
Flex your dates to find the best Santa Rosa-Chicago ticket prices. If you are flexible when it comes to your travel dates, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly to Chicago from Santa Rosa.
Set up a Price Alert. You can easily track the fare of your cheap Santa Rosa-Chicago flights by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
Fly without stops. Only interested in direct flights between Santa Rosa and Chicago? Make sure to tick 'Direct flights only' when performing a search. If there are direct flights available on the route, these will appear in the results.
Find the cheapest Business class flights from Santa Rosa and Chicago. We scour the internet for the best Business, Premium Economy and First Class flight fares to Chicago, too. Check the difference in price as you search – you might just chance upon a last-minute low fare. Note that not all cabin classes are available for every destination or airline.
Include nearby airports in your search. Widen your search for Santa Rosa to Chicago flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure point and your destination and could help you save next time you travel.

Combine your flight to Chicago from Santa Rosa with hotels and car hire

Once you've secured your cheap flight ticket from Santa Rosa to Chicago, discover the best prices and exclusive rates for hotels in Chicago or nearby. You can also compare hundreds of car hire companies in one go so that you get the best car hire price for your trip.