USD/US
Find cheap flights to Chicago, Illinois in 2026/2027 from $43 This is the cheapest return flight found to Chicago, Illinois from USA on FlightsFinder on October 20th 2026 at 10:55. This offer may no longer be available. Click the offer to check live prices & dates of travel.
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Our Flight Finder compares the cheapest flights to Chicago, Illinois from the most established flight comparison sites.
Fly to Chicago, Illinois and visit sites like Willis Tower, Navy Pier, Millennium Park & Cloud Gate.
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2. Compare the best Chicago, Illinois deals from top comparison engines
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These economy flights were found on FlightsFinder from USA to Chicago, Illinois in the last few days. Prices subject to availability.
These economy flights were found on FlightsFinder from USA to Chicago, Illinois in the last few days. Prices subject to availability.
According to our data, December is on average the cheapest time to book flights to Chicago, Illinois.
You can get flights from $43 return.
According to our data, September is on average the most expensive time to book flights to Chicago, Illinois.
A return flight could set you back more than $226.
Chicago, Illinois, fondly known as the "Windy City," is a vibrant metropolis that seamlessly blends tradition with innovation. From its iconic architecture showcasing the birthplace of the skyscraper to its rich cultural scene encompassing world-class museums, theaters, and music venues, Chicago offers a dynamic urban experience like no other. The city's diverse neighborhoods each have their own distinct character, from the historic charm of the Loop to the trendy vibes of Wicker Park. Renowned for its deep-dish pizza, passionate sports fans, and stunning waterfront views along Lake Michigan, Chicago invites visitors to explore its unique blend of history, culture, and modernity.
A good price for a flight to Chicago is $39 - $47.
The popular airports near Chicago, Illinois are O'Hare International Airport (ORD), Midway International Airport (MDW), and Chicago Rockford International Airport (RFD).
The flight to Chicago, Illinois (CHI) is roughly 1 hour 50 minutes and 606 miles (976 kilometres) from Atlanta, USA - Georgia, Atlanta Hartsfield-Jackson International Airport (ATL).
The best way is to compare flights to Chicago, Illinois from leading comparison sites using our search engine dashboard.
Yes, there are direct flights to Chicago, Illinois.
Here is the average weather forecast in Chicago, Illinois by month:
• Jan: 32°F
• Feb: 36°F
• Mar: 47°F
• Apr: 59°F
• May: 70°F
• Jun: 80°F
• Jul: 84°F
• Aug: 82°F
• Sep: 75°F
• Oct: 63°F
• Nov: 49°F
• Dec: 35°F
The main airport in Chicago, Illinois, O'Hare International Airport, is approximately 17 miles from the city center.
Typically, flights are cheapest to Chicago, Illinois 2 months before departure.
Studies show flights to Chicago, Illinois are typically cheaper on Tuesdays and Wednesdays.
64.6 °F
Thu, 29 Oct 2026
Average Temperature
32°F
Jan
36°F
Feb
47°F
Mar
59°F
Apr
70°F
May
80°F
Jun
84°F
Jul
82°F
Aug
75°F
Sep
63°F
Oct
49°F
Nov
35°F
Dec
Famously referred to the world over as the windy city, this metropolis lies adjacent to lake Michigan and is a vibrant and popular place.
Originally named the windy city after a commentary once made about it, the actual origin of the term is largely unknown and most believe it acquired its name because of the severe gales which swoop in from the surrounding lake.
Also sometimes refferred to as the 'second city' this land is one of the most populated in the whole of the United States of America. This is the reason it has acquired that name, as it was widely known as the second most populous area after New York.
Another explanation is that it was named the second city after it was rebuilt after the great fire of Chicago destroyed the entire location forcing the people to rebuild the entire area. This is conjectural however and the majority of people prefer the explanation given above.
The most popular tourist attraction in the city is Sears tower.
The amazing city of Chicago has practically something for every type of person – Whether you are into designer shopping, museums, cheap and cheerful unique neighbourhoods, art galleries or historical places of interest, Chicago will not disappoint.
Right adjacent to the lakefront, stretching from Oak Street Beach to the Gold Coast , the city is brimming with activities for one to do. Moreover there are numerous amusement parks, live concerts and riverboat casinos to select from.
It is near impossible to typecaste the people of this city. Whilst before it was infamous as a gangsters haven today it is home to first class theatres, amazing architecture and it is widely known for their abundance of sports enthusiasts.
Chicago has changed quite drastically over the last 50 or so years. Known nowadays as simply one of the finest cities of America, 3 million residents are know settled in what is now mostly known for the art and culture prevalent in the city.
Not fit to be known as the second city anymore, it is a popular place to hold opening events of major cultural occasions.
So what are you waiting for? find your cheap flights to Chicago now!
Happy Searching!
Cheap Flights Finder - Chicago Flights
Atlanta, USA - Georgia, Atlanta Hartsfield-Jackson International Airport (ATL) to Chicago, Illinois (CHI)
Distance:
606 miles (976 kilometres)
Average flight time (direct 1 hour 50 minutes)
Los Angeles, USA - California, Los Angeles International Airport (LAX) to Chicago, Illinois (CHI)
Distance:
1,741 miles (2,802 kilometres)
Average flight time (direct 4 hours 22 minutes)
New York, USA - John F Kennedy International Airport (JFK) to Chicago, Illinois (CHI)
Distance:
738 miles (1,188 kilometres)
Average flight time (direct 2 hours 8 minutes)
Dallas, USA - Dallas, Texas Fort Worth International Airport (DFW) to Chicago, Illinois (CHI)
Distance:
802 miles (1,290 kilometres)
Average flight time (direct 2 hours 16 minutes)
Denver, USA - Colorado, Airport - Denver International Airport (DEN) to Chicago, Illinois (CHI)
Distance:
886 miles (1,426 kilometres)
Average flight time (direct 2 hours 28 minutes)
San Francisco, USA - California, San Francisco International Airport (SFO) to Chicago, Illinois (CHI)
Distance:
1,842 miles (2,964 kilometres)
Average flight time (direct 4 hours 35 minutes)
Seattle, USA - Airport - Seattle Tacoma International, Washington (SEA) to Chicago, Illinois (CHI)
Distance:
1,716 miles (2,762 kilometres)
Average flight time (direct 4 hours 18 minutes)
Las Vegas, USA - Nevada, McCarran International Airport (LAS) to Chicago, Illinois (CHI)
Distance:
1,511 miles (2,431 kilometres)
Average flight time (direct 3 hours 51 minutes)
Orlando, USA - Florida, Orlando International Airport (MCO) to Chicago, Illinois (CHI)
Distance:
1,006 miles (1,620 kilometres)
Average flight time (direct 2 hours 44 minutes)
Charlotte, USA - North Carolina, Douglas International Airport (CLT) to Chicago, Illinois (CHI)
Distance:
599 miles (964 kilometres)
Average flight time (direct 1 hour 49 minutes)
Phoenix, USA - Arizona, Phoenix Sky Harbor International Airport (PHX) to Chicago, Illinois (CHI)
Distance:
1,437 miles (2,313 kilometres)
Average flight time (direct 3 hours 41 minutes)
Houston, USA - Texas, Airport - George Bush Intercontinental (IAH) to Chicago, Illinois (CHI)
Distance:
926 miles (1,490 kilometres)
Average flight time (direct 2 hours 33 minutes)
Miami, USA - Florida, Miami International Airport (MIA) to Chicago, Illinois (CHI)
Distance:
1,199 miles (1,930 kilometres)
Average flight time (direct 3 hours 9 minutes)
Boston, USA - Massachusetts, Edward L. Logan International Airport (BOS) to Chicago, Illinois (CHI)
Distance:
865 miles (1,391 kilometres)
Average flight time (direct 2 hours 25 minutes)
Minneapolis, USA - Minnesota, Airport - St. Paul International (MSP) to Chicago, Illinois (CHI)
Distance:
334 miles (537 kilometres)
Average flight time (direct 1 hour 14 minutes)
Fort Lauderdale, USA - Florida, Fort Lauderdale-Hollywood International Airport (FLL) to Chicago, Illinois (CHI)
Distance:
1,184 miles (1,905 kilometres)
Average flight time (direct 3 hours 7 minutes)
Detroit, USA - Michigan, Airport - Metropolitan Wayne County International (DTW) to Chicago, Illinois (CHI)
Distance:
234 miles (377 kilometres)
Average flight time (direct 1 hour 1 minute)
Philadelphia, USA - Pennsylvania, Airport - Philadelphia International (PHL) to Chicago, Illinois (CHI)
Distance:
676 miles (1,088 kilometres)
Average flight time (direct 2 hours)
Baltimore, USA - Maryland, Baltimore/Washington International Airport (BWI) to Chicago, Illinois (CHI)
Distance:
620 miles (998 kilometres)
Average flight time (direct 1 hour 52 minutes)
Salt Lake City, USA - Utah, Salt Lake City International Airport (SLC) to Chicago, Illinois (CHI)
Distance:
1,246 miles (2,006 kilometres)
Average flight time (direct 3 hours 16 minutes)
San Diego, USA - California, San Diego International Airport (SAN) to Chicago, Illinois (CHI)
Distance:
1,720 miles (2,768 kilometres)
Average flight time (direct 4 hours 19 minutes)
Tampa, USA - Florida, Tampa International Airport (TPA) to Chicago, Illinois (CHI)
Distance:
1,013 miles (1,631 kilometres)
Average flight time (direct 2 hours 45 minutes)
Portland, USA - International Airport, Oregon (PDX) to Chicago, Illinois (CHI)
Distance:
1,735 miles (2,792 kilometres)
Average flight time (direct 4 hours 21 minutes)
From Fort Lauderdale (FLL), USA to Chicago, United States (ORD): $43
Depart: 24 Dec 2026 · Return: 12 Jan 2027 Price found 20 Oct 2026, 10:55
From Philadelphia (PHL), USA to Chicago, United States (ORD): $54
Depart: 26 Feb 2027 · Return: 01 Mar 2027 Price found 28 Oct 2026, 23:19
From Denver (DEN), USA to Chicago, United States (ORD): $57
Depart: 03 Dec 2026 · Return: 05 Dec 2026 Price found 26 Oct 2026, 04:18
From Atlanta (ATL), USA to Chicago, United States (MDW): $57
Depart: 10 Nov 2026 · Return: 18 Nov 2026 Price found 27 Oct 2026, 12:34
From Washington D.C. (BWI), USA to Chicago, United States (ORD): $58
Depart: 19 Nov 2026 · Return: 03 Dec 2026 Price found 25 Oct 2026, 05:42
From Dallas (DFW), USA to Chicago, United States (MDW): $76
Depart: 17 Nov 2026 · Return: 16 Dec 2026 Price found 24 Oct 2026, 22:06
From Tampa (TPA), USA to Chicago, United States (ORD): $86
Depart: 24 Dec 2026 · Return: 05 Jan 2027 Price found 25 Oct 2026, 00:52
From Las Vegas (LAS), USA to Chicago, United States (RFD): $91
Depart: 07 Jan 2027 · Return: 10 Jan 2027 Price found 29 Oct 2026, 03:31
From Houston (IAH), USA to Chicago, United States (ORD): $106
Depart: 03 Dec 2026 · Return: 04 Dec 2026 Price found 25 Oct 2026, 09:31
From Minneapolis (MSP), USA to Chicago, United States (ORD): $109
Depart: 25 Dec 2026 · Return: 01 Jan 2027 Price found 28 Oct 2026, 19:30
From Miami (MIA), USA to Chicago, United States (ORD): $122
Depart: 10 Nov 2026 · Return: 14 Nov 2026 Price found 23 Oct 2026, 21:18
From Los Angeles (LAX), USA to Chicago, United States (ORD): $127
Depart: 05 Dec 2026 · Return: 08 Dec 2026 Price found 27 Oct 2026, 21:52
From Salt Lake City (SLC), USA to Chicago, United States (ORD): $137
Depart: 03 Dec 2026 · Return: 09 Dec 2026 Price found 26 Oct 2026, 19:36
From Charlotte (CLT), USA to Chicago, United States (ORD): $137
Depart: 24 Feb 2027 · Return: 01 Mar 2027 Price found 29 Oct 2026, 03:50
From San Diego (SAN), USA to Chicago, United States (ORD): $139
Depart: 03 Dec 2026 · Return: 06 Dec 2026 Price found 29 Oct 2026, 05:11
From Detroit (DTW), USA to Chicago, United States (ORD): $149
Depart: 14 Nov 2026 · Return: 16 Nov 2026 Price found 24 Oct 2026, 13:09
From San Francisco (SFO), USA to Chicago, United States (ORD): $167
Depart: 01 Dec 2026 · Return: 08 Dec 2026 Price found 21 Oct 2026, 17:14
From Boston (BOS), USA to Chicago, United States (MDW): $170
Depart: 18 Nov 2026 · Return: 23 Nov 2026 Price found 21 Oct 2026, 20:40
From Seattle (SEA), USA to Chicago, United States (ORD): $176
Depart: 14 Nov 2026 · Return: 14 Dec 2026 Price found 20 Oct 2026, 19:06
From Portland (PDX), USA to Chicago, United States (ORD): $212
Depart: 10 Dec 2026 · Return: 15 Dec 2026 Price found 21 Oct 2026, 22:27
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