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Cheap Flights from Greenville (GSP) to Chicago (CHIA)

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      Compare Greenville-Spartanburg to Chicago flight deals

      Find the cheapest month or even day of the year to fly to Chicago

      Book the best Chicago fare with no extra fees

      Flight deals from Greenville-Spartanburg to Chicago

      Looking for a cheap last-minute deal or the best return flight from Greenville-Spartanburg Airport to Chicago? If you want to travel next month, return fares start from $450. Find the lowest prices on one-way and return tickets right here.
      Chicago.$313 per passenger.Departing Wed, 9 Dec, returning Sat, 12 Dec.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Greenville-Spartanburg on Wed, 9 Dec, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sat, 12 Dec, arriving in Greenville-Spartanburg.Price includes taxes and charges.From $313, select.
      Chicago.$430 per passenger.Departing Wed, 3 Feb, returning Sun, 7 Feb.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Greenville-Spartanburg on Wed, 3 Feb, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 7 Feb, arriving in Greenville-Spartanburg.Price includes taxes and charges.From $430, select.
      Chicago.$445 per passenger.Departing Fri, 9 Apr, returning Fri, 23 Apr.Return flight with United.Outbound direct flight with United departs from Greenville-Spartanburg on Fri, 9 Apr, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Fri, 23 Apr, arriving in Greenville-Spartanburg.Price includes taxes and charges.From $445, select.
      Chicago.$447 per passenger.Departing Fri, 5 Mar, returning Sun, 7 Mar.Return flight with United.Outbound direct flight with United departs from Greenville-Spartanburg on Fri, 5 Mar, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sun, 7 Mar, arriving in Greenville-Spartanburg.Price includes taxes and charges.From $447, select.
      Chicago.$447 per passenger.Departing Sat, 31 Oct, returning Mon, 23 Nov.Return flight with United.Outbound direct flight with United departs from Greenville-Spartanburg on Sat, 31 Oct, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Mon, 23 Nov, arriving in Greenville-Spartanburg.Price includes taxes and charges.From $447, select.
      Chicago.$448 per passenger.Departing Wed, 3 Feb, returning Sun, 7 Feb.Return flight with United.Outbound direct flight with United departs from Greenville-Spartanburg on Wed, 3 Feb, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sun, 7 Feb, arriving in Greenville-Spartanburg.Price includes taxes and charges.From $448, select.
      Chicago.$448 per passenger.Departing Thu, 27 May, returning Sat, 29 May.Return flight with United.Outbound direct flight with United departs from Greenville-Spartanburg on Thu, 27 May, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 29 May, arriving in Greenville-Spartanburg.Price includes taxes and charges.From $448, select.
      Chicago.$448 per passenger.Departing Fri, 4 Jun, returning Sun, 6 Jun.Return flight with United.Outbound direct flight with United departs from Greenville-Spartanburg on Fri, 4 Jun, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sun, 6 Jun, arriving in Greenville-Spartanburg.Price includes taxes and charges.From $448, select.
      Chicago.$448 per passenger.Departing Thu, 10 Dec, returning Sun, 13 Dec.Return flight with United.Outbound direct flight with United departs from Greenville-Spartanburg on Thu, 10 Dec, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sun, 13 Dec, arriving in Greenville-Spartanburg.Price includes taxes and charges.From $448, select.
      Chicago.$450 per passenger.Departing Thu, 5 Nov, returning Sun, 8 Nov.Return flight with United.Outbound direct flight with United departs from Greenville-Spartanburg on Thu, 5 Nov, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sun, 8 Nov, arriving in Greenville-Spartanburg.Price includes taxes and charges.From $450, select.
      Chicago.$450 per passenger.Departing Mon, 18 Jan, returning Mon, 1 Feb.Return flight with United.Outbound direct flight with United departs from Greenville-Spartanburg on Mon, 18 Jan, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Mon, 1 Feb, arriving in Greenville-Spartanburg.Price includes taxes and charges.From $450, select.
      Chicago.$450 per passenger.Departing Thu, 15 Oct, returning Mon, 19 Oct.Return flight with United.Outbound direct flight with United departs from Greenville-Spartanburg on Thu, 15 Oct, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Mon, 19 Oct, arriving in Greenville-Spartanburg.Price includes taxes and charges.From $450, select.
      Chicago.$451 per passenger.Departing Mon, 23 Nov, returning Mon, 7 Dec.Return flight with United.Outbound direct flight with United departs from Greenville-Spartanburg on Mon, 23 Nov, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Mon, 7 Dec, arriving in Greenville-Spartanburg.Price includes taxes and charges.From $451, select.
      Chicago.$461 per passenger.Departing Sun, 3 Jan, returning Sun, 17 Jan.Return flight with United.Outbound indirect flight with United, departs from Greenville-Spartanburg on Sun, 3 Jan, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Sun, 17 Jan, arriving in Greenville-Spartanburg.Price includes taxes and charges.From $461, select.
      Chicago.$482 per passenger.Departing Sat, 12 Dec, returning Mon, 11 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Greenville-Spartanburg on Sat, 12 Dec, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 11 Jan, arriving in Greenville-Spartanburg.Price includes taxes and charges.From $482, select.
      Chicago.$569 per passenger.Departing Sat, 26 Sep, returning Sat, 3 Oct.Return flight with United.Outbound direct flight with United departs from Greenville-Spartanburg on Sat, 26 Sep, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 3 Oct, arriving in Greenville-Spartanburg.Price includes taxes and charges.From $569, select.
      How did we find these deals? The deals you see here are the lowest prices for flight tickets from Greenville-Spartanburg to Chicago found in the last 4 days, and are subject to change and availability.

      Find the cheapest month to fly from Greenville-Spartanburg to Chicago

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Greenville-Spartanburg to Chicago flights are currently cheapest in December.
      Sep
      from $570
      Oct
      from $450
      Nov
      from $450
      Dec
      from $313
      Jan
      from $461
      Feb
      from $430
      Mar
      from $447
      Apr
      from $445
      May
      from $448
      Jun
      from $448
      Jul
      Find prices
      Aug
      Find prices

      Direct flights from Greenville-Spartanburg to Chicago

      Air Canada
      Air New Zealand
      Alaska Airlines
      American Airlines
      ANA (All Nippon Airways)
      Avianca
      Emirates
      Envoy Air
      GoJet Airlines
      Lufthansa
      PSA Airlines
      Qatar Airways
      Republic Airways
      SkyWest Airlines
      United

      Alternative Greenville-Spartanburg to Chicago routes

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

      Chicago Midway

      14km from central Chicago
      ClosestCheapest
      from $314
      Search flights

      Chicago O'Hare International

      25km from central Chicago
      from $445
      Search flights

      Chicago Rockford

      127km from central Chicago
      Search flights

      Greenville to Chicago: Flight information

      The things to know before you go.
      Cheapest flight found$313
      Cheapest month to flyDecember
      Average flight time2 hrs, 21 mins
      Most popular airlineAmerican Airlines
      Average flights per week723

      Finding cheap flights from Greenville-Spartanburg to Chicago: Frequently asked questions

      There are 3 airports in Chicago: Chicago Midway, Chicago O'Hare International and Chicago Rockford.
      The best price we found for a return flight from Greenville-Spartanburg to Chicago is $313. 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.
      2 hours and 21 minutes is the average flight time from Greenville-Spartanburg to Chicago.
      American Airlines, Alaska Airlines and United fly direct from Greenville-Spartanburg to Chicago.
      As of September 2026, there are 241 flights per week flying from Greenville-Spartanburg to Chicago.
      The cheapest month to fly from Greenville-Spartanburg to Chicago is usually December.
      If you're flying from Greenville-Spartanburg Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from $313.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Greenville-Spartanburg Airport to Chicago on Wednesday, 9 December 2026.
      Yes – the average flight time is 2 hours and 21 minutes.
      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.

      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.

      In September, the average temperature is usually around 20°C. July is typically the warmest month in Chicago, when it usually averages around 27°C. You can expect the least rain in February. The coldest month is January, with temperatures averaging -5°C. The rainiest month is June.
      Currently, Southwest Airlines and United offer the cheapest flight tickets to Chicago.

      Flying from Greenville-Spartanburg International Airport (GSP) to Chicago: what you need to know

      • The average duration of a direct flight from Greenville-Spartanburg International Airport to Chicago is 1 hour 55 minutes.

      • Chicago is one hour behind Greenville, where Greenville-Spartanburg International Airport is located. Chicago runs on the UTC-6 timezone.

      • Greenville-Spartanburg International Airport (GSP) to Chicago O'Hare International Airport (ORD) is the most popular route, with 39 departures a week to choose from. If you prefer starting your day later, the last flight from GSP to ORD is with American Airlines at 18:46. Opt for the first departure operated by United Airlines at 06:30 if you want to fly out earlier.

      • To avoid rushing for your GSP to Chicago flight, leave enough time for things like check-in and baggage drop. Turning up two hours ahead of international departures and one hour before domestic flights is the general rule.

      • During popular months like July, you'll want to get to the airport even earlier. Arrive two hours before domestic departures and four hours ahead of an international flight when you fly during peak periods in general.

      • Direct Greenville-Spartanburg International Airport to Chicago tickets are available for booking. Chicago O'Hare International Airport (ORD) will be where your journey ends.

      • Keep an eye out for offers from United Airlines. This airline has direct flights from Greenville-Spartanburg International Airport to Chicago.

      • Located around 16 kilometres from the centre of Greenville, GSP can be reached in about 25 minutes by car, depending on traffic. The journey on public transport takes roughly 50 minutes.

      • Have an early flight from Greenville-Spartanburg International Airport to Chicago? Avoid the hassle of rushing to the terminal (and enjoy a little extra shut-eye) by choosing one of these hotels near GSP:

      • When it comes to Greenville-Spartanburg International Airport's on-time performance, 79% of flights stick to their scheduled arrival time.

      • GSP is located at 2000 GPS Drive, Suite 1.

      How to find the cheapest flights from Greenville-Spartanburg International Airport (GSP) to Chicago

      • $157 is the lowest price we've seen for a one-way Greenville-Spartanburg International Airport to Chicago flight. A round-trip ticket right now is $313. Depending on when and how early you book, these fares may change.

      • Book one month before your departure date. Pricing trends suggest that this is the ideal window for finding cheap flights from GSP to Chicago.

      • Plan your trip for June. That's the best month for landing the biggest deals on Greenville-Spartanburg International Airport to Chicago tickets. If you're flexible with your dates, use the 'Whole month' tool to find the cheapest price across each month.

      • Picking up a cheap flight from GSP to Chicago is easy with Price Alerts. Simply create one of these automatic notifications and we'll get in touch as soon as the price has dropped.

      • Pick your preferred arrival and departure times, number of stops and airlines with our filters. Then, sort the results for your flight from Greenville-Spartanburg International Airport to Chicago by 'Cheapest,' 'Best' or 'Fastest.'

      Airports in Chicago

      Chicago O'Hare International Airport (ORD)

      • Chicago O'Hare International Airport (ORD) is around 27 kilometres from central Chicago. If you're grabbing a taxi or a ride-share, the drive takes about 30 minutes.

      • Getting there on public transport takes around 45 minutes.

      • Book a hotel close to ORD if you have a late flight from Greenville-Spartanburg International Airport to Chicago. Select one of these accommodation options and make your arrival easier:

      • Reserving your vehicle from Chicago O'Hare International Airport around four weeks before your flight from GSP to Chicago can help you lock in the lowest rate.

      • ORD is located at 10000 West O'Hare.

      Chicago Midway International Airport (MDW)

      • After your flight from Greenville-Spartanburg International Airport to Chicago has arrived, you can get to the city centre in around 25 minutes by car. Central Chicago is roughly 16 kilometres from Chicago Midway International Airport (MDW).

      • The journey will take about 30 minutes on public transport.

      • Following your GSP to Chicago flight, kick back at a hotel close to MDW. These are some great accommodation options that'll help you slip into relaxation mode:

      • Don't pay more than you need to. Booking your ride four weeks before your arrival at MDW will save you money.

      • The address for Chicago Midway International Airport is 5700 South Cicero.

      Chicago Rockford International Airport (RFD)

      • Step off your flight from Greenville-Spartanburg International Airport to Chicago and head for your hotel or jump right into sightseeing. The centre of Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and typically takes 1 hour 40 minutes to reach by car.

      • The journey takes around 2 hours using public transport.

      • Enjoy a low-stress, comfortable start to your break by checking in to a hotel near RFD after your GSP to Chicago flight. Unwind after a day of travel or just give yourself time to get your bearings in a new destination at:

      • If you're hoping for a particular make or model, booking early gives you a better shot at getting exactly what you want. Reserve your ride from RFD a few weeks ahead of your flight from Greenville-Spartanburg International Airport to Chicago.

      • Chicago Rockford International Airport's official address is 2 Airport Cir.

      Best time to go to Chicago

      • July is the most popular month for flights from Greenville-Spartanburg International Airport to Chicago. To escape the crowds, plan your trip to Chicago in January.

      • The warmest month in Chicago is July, with temperatures ranging between 16ºC (61ºF) and 28ºC (82ºF). Lock in your Greenville-Spartanburg International Airport to Chicago plane ticket then if you enjoy this type of weather.

      • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for a cheap ticket from GSP to Chicago around that time if you'd rather travel in cooler conditions.

      More about Chicago

      • Once you've booked your flight from Greenville-Spartanburg International Airport to Chicago, find a hotel that offers the right mix of comfort and location. Make one of these options your base for exploring Chicago:

      • There are so many things to do and see in this city it can be tricky to work out where to start. Art Institute of Chicago, Millennium Park and Willis Tower are popular attractions which should feature on any good Chicago itinerary.

      Explore more of the United States

      • Columbus is just one of the many cities in the United States waiting to be explored once you've seen Chicago. Around 451 kilometres away to the southeast, check out popular attractions including Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

      • Around 257 kilometres southeast of Chicago, Indianapolis is another essential stop in the United States. Experience the best of this destination with a visit to Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

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      Plan the rest of your trip from Greenville to Chicago

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.