Cheap flights from Santa Rosa to Chicago

Flights overview

Useful information for finding cheap flights from Santa Rosa to Chicago and booking your next trip
Cheapest round-trip flights $331
American 1 stop 7 hr Thu, May 28 — Wed, Jun 3
The cheapest round-trip flight from Santa Rosa to Chicago is currently $331
Cheapest one-way flight $152
American 1 stop 9 hr Wed, May 27
The cheapest one-way flight from Santa Rosa to Chicago is currently $152
Last-minute weekend getaway $786
Southwest 2 stops 10 hr Sat, May 9 — Mon, May 11
The cheapest last-minute weekend getaway from Santa Rosa to Chicago is currently $786
Cheapest business class flights $1,033
Alaska 1 stop 15 hr Sat, May 30 — Sat, Jun 6
The cheapest business class round-trip flight from Santa Rosa to Chicago is currently $1,033
Fastest flight 5 hr 50 min The fastest flight with stops from Santa Rosa to Chicago takes 5 hr 50 min
Nonstop flights None There are no direct flights on this route.

When is the cheapest time to fly?

The cheapest month to fly from Santa Rosa to Chicago is typically January. The most expensive month to fly is typically March.
January
Cheapest
Typical prices: $295–570
March
Most expensive
Typical prices: $345–740

Popular airlines from Santa Rosa to Chicago

  • Southwest
    from $365
    Typical price: $415–590
    2253 weekly connecting flights
    STS - MDW, ORD Every day
  • American
    from $331
    Typical price: $475–840
    80 weekly connecting flights
    STS - ORD Every day
  • Alaska
    from $356
    Typical price: $335–740
    73 weekly connecting flights
    STS - ORD Every day

Popular airports near Santa Rosa

  • San Francisco International Airport (SFO)
    San Francisco United States 1 hr 19 min 59 mi
  • Charles M. Schulz–Sonoma County Airport (STS)
    Santa Rosa United States 12 min 7 mi
  • Oakland San Francisco Bay Airport (OAK)
    Oakland United States 1 hr 10 min 56 mi
  • Sacramento International Airport (SMF)
    Sacramento United States 1 hr 47 min 63 mi

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 26 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 23 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from Santa Rosa to Chicago

The cheapest flights from Santa Rosa to Chicago are usually in January. Typical ticket prices in January range from $295 to $570.
The cheapest round-trip flight from Santa Rosa to Chicago recently found on Google Flights was with American from $331. The cheapest one-way flight was with American from $152.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from Santa Rosa to Chicago is $365, flying from May 30 to Jun 6.
  • The cheapest American flight from Santa Rosa to Chicago is $331, flying from May 28 to Jun 3.
  • The cheapest Alaska flight from Santa Rosa to Chicago is $356, flying from May 30 to Jun 5.
The cheapest round-trip flight from Santa Rosa to Chicago starts at $331 from Thu, May 28 to Wed, Jun 3. The cheapest one-way flight starts at $152 and departs on Wed, May 27.
5 hr 50 min is the shortest flight time from Santa Rosa to Chicago.
Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.
It's easy to use Google Flights to find the cheapest days to fly from Santa Rosa to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from Santa Rosa to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Santa Rosa to Chicago.

In terms of flights, Southwest is the most popular. Southwest offers 2,253 connecting flights per week. Southwest flies from Charles M. Schulz–Sonoma County Airport (STS) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from Santa Rosa to Chicago are:
  • American offers 80 connecting flights per week. American flies from Charles M. Schulz–Sonoma County Airport (STS) to Chicago O'Hare International Airport (ORD) .
  • Alaska offers 73 connecting flights per week. Alaska flies from Charles M. Schulz–Sonoma County Airport (STS) to Chicago O'Hare International Airport (ORD) .
The number of connecting flights refers to distinct flights with at least one stop between Santa Rosa and Chicago.
The cheapest round-trip flight from Santa Rosa to Chicago recently found on Google Flights was with American from $331. The cheapest one-way flight was with American from $152.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest Southwest flight from Santa Rosa to Chicago is $365, flying from May 30 to Jun 6.
  • The cheapest American flight from Santa Rosa to Chicago is $331, flying from May 28 to Jun 3.
  • The cheapest Alaska flight from Santa Rosa to Chicago is $356, flying from May 30 to Jun 5.
No airline flies direct from Santa Rosa to Chicago.
  • There are 2253 Southwest connecting flights from Santa Rosa to Chicago per week. Flights are available every day.
  • There are 80 American connecting flights from Santa Rosa to Chicago per week. Flights are available every day.
  • There are 73 Alaska connecting flights from Santa Rosa to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
The cheapest last-minute deal between Santa Rosa and Chicago at price $786 is offered by Southwest from Sat, May 9 to Mon, May 11.
No airline flies direct from Santa Rosa to Chicago.
  • There are 2253 Southwest connecting flights from Santa Rosa to Chicago per week. Flights are available every day.
  • There are 80 American connecting flights from Santa Rosa to Chicago per week. Flights are available every day.
  • There are 73 Alaska connecting flights from Santa Rosa to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
There are no direct flights from Santa Rosa to Chicago.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Santa Rosa to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between Santa Rosa and Chicago start at $1,033 from Sat, May 30 to Sat, Jun 6 with Alaska.
The cheapest economy class round-trip flights between Santa Rosa and Chicago start at $331 from Thu, May 28 to Wed, Jun 3.
To book business class trips from Santa Rosa to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between Santa Rosa and Chicago starts at $786 from Sat, May 9 to Mon, May 11 with Southwest.
The cheapest last-minute deal between Santa Rosa and Chicago at price $786 is offered by Southwest from Sat, May 9 to Mon, May 11.
To find last-minute flight deals from Santa Rosa to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

Search more flights

Popular trips from Santa Rosa

  1. Seattle
    $217
    May 23 — May 30
    Nonstop 1 hr 59 min Alaska
  2. Las Vegas
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    Nonstop 1 hr 47 min Alaska
  3. London
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  4. Paris
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