Cheap Flights from Sarasota to Chicago from $165

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Flight deals from Sarasota to Chicago

Looking for a cheap last-minute deal or the best return flight from Sarasota Airport to Chicago? If you want to travel next month, return fares start from $249. Find the lowest prices on one-way and return tickets right here.

Chicago.$165 per passenger.Departing Wed, 12 Aug, returning Sat, 15 Aug.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Sarasota on Wed, 12 Aug, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Sat, 15 Aug, arriving in Sarasota.Price includes taxes and charges.From $165, select.

Chicago.$182 per passenger.Departing Sun, 20 Sep, returning Sun, 27 Sep.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Sarasota on Sun, 20 Sep, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Sun, 27 Sep, arriving in Sarasota.Price includes taxes and charges.From $182, select.

Chicago.$192 per passenger.Departing Wed, 29 Jul, returning Sat, 15 Aug.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Sarasota on Wed, 29 Jul, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Sat, 15 Aug, arriving in Sarasota.Price includes taxes and charges.From $192, select.

Chicago.$192 per passenger.Departing Thu, 27 Aug, returning Sun, 6 Sep.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Sarasota on Thu, 27 Aug, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Sun, 6 Sep, arriving in Sarasota.Price includes taxes and charges.From $192, select.

Chicago.$217 per passenger.Departing Sat, 18 Jul, returning Sat, 25 Jul.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Sarasota on Sat, 18 Jul, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Sat, 25 Jul, arriving in Sarasota.Price includes taxes and charges.From $217, select.

Chicago.$224 per passenger.Departing Sun, 20 Sep, returning Sun, 4 Oct.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Sarasota on Sun, 20 Sep, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Sun, 4 Oct, arriving in Sarasota.Price includes taxes and charges.From $224, select.

Chicago.$231 per passenger.Departing Thu, 12 Nov, returning Sun, 15 Nov.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Sarasota on Thu, 12 Nov, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Sun, 15 Nov, arriving in Sarasota.Price includes taxes and charges.From $231, select.

Chicago.$232 per passenger.Departing Sat, 20 Jun, returning Sat, 4 Jul.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Sarasota on Sat, 20 Jun, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Sat, 4 Jul, arriving in Sarasota.Price includes taxes and charges.From $232, select.

Chicago.$249 per passenger.Departing Sat, 20 Jun, returning Sat, 27 Jun.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Sarasota on Sat, 20 Jun, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Sat, 27 Jun, arriving in Sarasota.Price includes taxes and charges.From $249, select.

Chicago.$260 per passenger.Departing Thu, 1 Oct, returning Thu, 15 Oct.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Sarasota on Thu, 1 Oct, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Thu, 15 Oct, arriving in Sarasota.Price includes taxes and charges.From $260, select.

Chicago.$402 per passenger.Departing Tue, 20 Oct, returning Tue, 3 Nov.Return flight with United.Outbound direct flight with United departs from Sarasota on Tue, 20 Oct, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 3 Nov, arriving in Sarasota.Price includes taxes and charges.From $402, select.

Chicago.$472 per passenger.Departing Sat, 30 May, returning Wed, 17 Jun.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Sarasota on Sat, 30 May, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Wed, 17 Jun, arriving in Sarasota.Price includes taxes and charges.From $472, select.

Chicago.$487 per passenger.Departing Thu, 19 Nov, returning Thu, 3 Dec.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Sarasota on Thu, 19 Nov, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Thu, 3 Dec, arriving in Sarasota.Price includes taxes and charges.From $487, select.

Chicago.$540 per passenger.Departing Thu, 10 Dec, returning Sun, 20 Dec.Return flight with Allegiant Air.Outbound direct flight with Allegiant Air departs from Sarasota on Thu, 10 Dec, arriving in Chicago Rockford.Inbound direct flight with Allegiant Air departs from Chicago Rockford on Sun, 20 Dec, arriving in Sarasota.Price includes taxes and charges.From $540, select.

Chicago.$578 per passenger.Departing Tue, 23 Feb, returning Tue, 2 Mar.Return flight with American Airlines.Outbound direct flight with American Airlines departs from Sarasota on Tue, 23 Feb, arriving in Chicago O'Hare International.Inbound direct flight with American Airlines departs from Chicago O'Hare International on Tue, 2 Mar, arriving in Sarasota.Price includes taxes and charges.From $578, select.

Chicago.$656 per passenger.Departing Wed, 27 May, returning Sat, 30 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Sarasota on Wed, 27 May, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Sat, 30 May, arriving in Sarasota.Price includes taxes and charges.From $656, select.

Find the cheapest month to fly from Sarasota to Chicago

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

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Direct flights from Sarasota to Chicago

Alternative Sarasota to Chicago routes

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

Sarasota to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$165
Cheapest month to fly	August
Average flight time	2 hrs, 57 mins
Most popular airline	American Airlines
Average flights per week	93

Finding cheap flights from Sarasota 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 Sarasota to Chicago?

The best price we found for a return flight from Sarasota to Chicago is $165. 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.

How long does it take to fly from Sarasota to Chicago?

2 hours and 57 minutes is the average flight time from Sarasota to Chicago.

Which airlines fly direct from Sarasota to Chicago?

American Airlines, United and Southwest Airlines fly direct from Sarasota to Chicago.

How many flights are there a week from Sarasota to Chicago?

As of May 2026, there are 93 flights per week flying from Sarasota to Chicago.

When is the cheapest time to fly from Sarasota to Chicago?

The cheapest month to fly from Sarasota to Chicago is usually August.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Sarasota Airport, the cheapest airport near Chicago is Chicago Rockford – which is 126.2 km away from the centre of Chicago. We've found flights into this airport from $165.

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

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Sarasota Airport to Chicago on Wednesday, 12 August 2026.

Can I get a direct flight from Sarasota Airport to Chicago?

Yes – the average flight time is 2 hours and 57 minutes.

How can I get the best flight deal from Sarasota 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 May, the average temperature is usually around 13°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 Sarasota Airport to Chicago with?

Currently, Allegiant Air offers the cheapest flight tickets to Chicago.

Travelling from Sarasota Bradenton International Airport (SRQ) to Chicago: what you need to know

The average time for a direct flight from Sarasota Bradenton International Airport to Chicago is 2 hours 55 minutes.
Sarasota Bradenton International Airport is located in Sarasota. Based in the UTC-6 timezone, Chicago is one hour behind Sarasota.
The most popular route is from Sarasota Bradenton International Airport (SRQ) to Chicago O'Hare International Airport (ORD). Choose from 17 weekly services between these two airports. If you'd like to get on your way as soon as possible, the earliest flight from SRQ to ORD is the 07:20 United Airlines service. If you prefer to leave later in the day, the last departure is at 18:05 with United Airlines.
To avoid missing your SRQ to Chicago flight, leave plenty of time for things like check-in and baggage drop. Arriving two hours before international departures and an hour before domestic flights is the general rule.
During popular months like March, it's wise to get to the airport even earlier. Arrive two hours before a domestic departure and four hours ahead of international flights whenever you're travelling during a peak period in general.
You can travel nonstop from SRQ to Chicago. Pick from these arrival points when searching for a Sarasota Bradenton International Airport to Chicago ticket:
- Chicago O'Hare International Airport (ORD)
- Chicago Midway International Airport (MDW)
- Chicago Rockford International Airport (RFD)
You'll have your choice of carriers that offer direct flights from Sarasota Bradenton International Airport to Chicago. Book your journey with one of these:
Travelling from central Sarasota to SRQ takes about 35 minutes by public transport. If you drive, ride-share or get a taxi, you'll cover the 6 kilometres in 15 minutes or so, depending on traffic conditions.
Searching for a hotel close to SRQ? If you're catching an early flight from Sarasota Bradenton International Airport to Chicago, these accommodation options put the terminal practically at your doorstep:
Sarasota Bradenton International Airport has an excellent on-time record, so flight disruptions are less likely. Departures from SRQ arrive on schedule 80% of the time.
SRQ is located at 6000 Airport Circle.

How to find the cheapest flights from Sarasota Bradenton International Airport (SRQ) to Chicago

The lowest price we've seen for a one-way Sarasota Bradenton International Airport to Chicago flight is $70. The cheapest price for a return flight is $165. Bear in mind fares may change due to availability at the time of booking.
To pick up cheap flights from SRQ to Chicago, book early. Airlines tend to offer their most competitively priced fares when flights first go on sale.
The 'Whole month' tool will show you the cheapest tickets from Sarasota Bradenton International Airport to Chicago throughout the entire month. It's an easy way to snap up a bargain if your trip dates are flexible.
Save time looking for cheap flights from SRQ to Chicago by creating a Price Alert. You'll get an email or notification on the app when fares go down.
Choose your ideal arrival and departure times, number of stops and airlines with our filters. Then, sort the results for your flight from Sarasota Bradenton International Airport to Chicago by 'Best,' 'Cheapest' or 'Fastest.'

Airports in Chicago

Chicago O'Hare International Airport (ORD)

Chicago O'Hare International Airport (ORD) to the centre of Chicago takes around 30 minutes by car. The centre is roughly 27 kilometres away.
It'll take around 45 minutes if you're travelling on public transport.
If you have a late flight from Sarasota Bradenton International Airport to Chicago, few things beat the convenience of staying close to the terminal. Grab your bags from the carousel and then be showered and relaxing not long after at one of these hotels near ORD:
Reserving your vehicle from Chicago O'Hare International Airport around four weeks in advance of your flight from SRQ to Chicago can help you lock in the lowest rate.
You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

Chicago Midway International Airport (MDW) is around 16 kilometres from central Chicago. Once you've hopped off your flight from Sarasota Bradenton International Airport to Chicago, it'll take you around 25 minutes to reach the heart of the city in a ride-share or taxi.
If you're travelling on public transport, it'll take about 30 minutes.
Hang the 'Do not disturb' sign on your door and rest at a hotel close to MDW. Here are a few options where you can kick back after your SRQ to Chicago flight:
Get exactly what you want. Securing your ride from MDW four weeks in advance often means better deals and a greater range of vehicles.
The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Make your way to the city centre after your flight from Sarasota Bradenton International Airport to Chicago has touched down. Central Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 40 minutes to reach by taxi or ride-share.
Public transport can take you there in about 2 hours.
Choose a hotel close to RFD and go from landing to lounging in your room in a flash. Whether you're coming in on a late SRQ to Chicago flight or just want a hassle-free arrival, these stays bring comfort closer to you:
Rental agencies sometimes offer discounts on early bookings, so reserve your vehicle from RFD in advance of your flight from Sarasota Bradenton International Airport to Chicago. A little planning can save you money.
Chicago Rockford International Airport's street address is 2 Airport Cir.

Best time to go to Chicago

It's time to pick your travel dates for your flight from Sarasota Bradenton International Airport to Chicago. July is the most popular month to travel to Chicago. If you want a quieter atmosphere, go in January.
Before booking a Sarasota Bradenton International Airport to Chicago plane ticket, think about the kind of weather forecast you're hoping for. July is the warmest month in Chicago, with temperatures ranging from 16ºC to 28ºC.
Look for cheap tickets from SRQ to Chicago in January if you'd rather travel during cooler conditions. Temperatures are at their lowest then, ranging between -12ºC and 3ºC on average.

More about Chicago

When it comes to looking for somewhere to lay your head, you'll find the best stays in Chicago right here. Check out these options after you've booked your flight from Sarasota Bradenton International Airport to Chicago:
Art Institute of Chicago and Millennium Park are just the start of the top attractions to add to your Chicago itinerary. Continue your sightseeing adventures at Willis Tower.

Explore more of the United States

Chicago has plenty to offer, but there are so many other parts of the United States just waiting to be explored. About 451 kilometres southeast of Chicago, a visit to Columbus will keep your itinerary packed. Start with leading attractions like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.
If you're ready to explore another great destination in the United States, consider Indianapolis, roughly 257 kilometres southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are key reasons to visit.