USD/US
Find cheap flights to Chicago, Illinois in 2025/2026 from $50 This is the cheapest return flight found to Chicago, Illinois from USA on FlightsFinder on July 10th 2025 at 00:57. This offer may no longer be available. Click the offer to check live prices & dates of travel.
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.
1. Enter your search requirements for Chicago, Illinois
2. Compare the best Chicago, Illinois deals from top comparison engines
3. Book your Chicago, Illinois flight at the cheapest price
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, August is on average the cheapest time to book flights to Chicago, Illinois.
You can get flights from $50 return.
According to our data, June is on average the most expensive time to book flights to Chicago, Illinois.
A return flight could set you back more than $229.
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.
67.9 °F
Thu, 10 Jul 2025
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 Detroit (DTW), USA to Chicago, United States (MDW): $60
Depart: 05 Aug 2025 · Return: 20 Aug 2025 Price found 07 Jul 2025, 14:04
From Atlanta (ATL), USA to Chicago, United States (ORD): $62
Depart: 05 Aug 2025 · Return: 06 Aug 2025 Price found 09 Jul 2025, 16:48
From Boston (BOS), USA to Chicago, United States (MDW): $79
Depart: 04 Sep 2025 · Return: 08 Sep 2025 Price found 10 Jul 2025, 05:02
From Washington D.C. (BWI), USA to Chicago, United States (ORD): $84
Depart: 07 Sep 2025 · Return: 11 Sep 2025 Price found 08 Jul 2025, 02:40
From Las Vegas (LAS), USA to Chicago, United States (ORD): $85
Depart: 05 Aug 2025 · Return: 24 Aug 2025 Price found 09 Jul 2025, 19:48
From New York (JFK), USA to Chicago, United States (ORD): $85
Depart: 04 Sep 2025 · Return: 04 Sep 2025 Price found 09 Jul 2025, 23:13
From Fort Lauderdale (FLL), USA to Chicago, United States (ORD): $87
Depart: 05 Aug 2025 · Return: 06 Aug 2025 Price found 09 Jul 2025, 20:38
From Dallas (DFW), USA to Chicago, United States (ORD): $87
Depart: 19 Sep 2025 · Return: 21 Sep 2025 Price found 10 Jul 2025, 03:13
From Miami (MIA), USA to Chicago, United States (ORD): $87
Depart: 30 Jul 2025 · Return: 05 Aug 2025 Price found 10 Jul 2025, 05:02
From Seattle (SEA), USA to Chicago, United States (ORD): $88
Depart: 12 Aug 2025 · Return: 16 Aug 2025 Price found 09 Jul 2025, 21:13
From Portland (PDX), USA to Chicago, United States (ORD): $88
Depart: 21 Aug 2025 · Return: 26 Aug 2025 Price found 10 Jul 2025, 04:44
From Denver (DEN), USA to Chicago, United States (ORD): $89
Depart: 03 Oct 2025 · Return: 05 Oct 2025 Price found 09 Jul 2025, 22:22
From Minneapolis (MSP), USA to Chicago, United States (MDW): $91
Depart: 04 Aug 2025 · Return: 05 Aug 2025 Price found 09 Jul 2025, 16:51
From Los Angeles (LAX), USA to Chicago, United States (ORD): $91
Depart: 02 Aug 2025 · Return: 05 Aug 2025 Price found 10 Jul 2025, 05:57
From San Diego (SAN), USA to Chicago, United States (MDW): $104
Depart: 30 Sep 2025 · Return: 04 Oct 2025 Price found 08 Jul 2025, 07:07
From Philadelphia (PHL), USA to Chicago, United States (ORD): $105
Depart: 22 Sep 2025 · Return: 26 Sep 2025 Price found 08 Jul 2025, 14:35
From San Francisco (SFO), USA to Chicago, United States (MDW): $105
Depart: 01 Nov 2025 · Return: 05 Nov 2025 Price found 08 Jul 2025, 15:31
From Charlotte (CLT), USA to Chicago, United States (ORD): $108
Depart: 14 Nov 2025 · Return: 17 Nov 2025 Price found 06 Jul 2025, 23:09
From Salt Lake City (SLC), USA to Chicago, United States (ORD): $143
Depart: 04 Aug 2025 · Return: 06 Aug 2025 Price found 08 Jul 2025, 13:10
GBP/UK
EUR/Ireland
AUD/Australia
CAD/Canada
INR/India
AED/United Arab Emirates
HKD/Hong Kong
ILS/Israel
MYR/Malaysia
NZD/New Zealand
PHP/Philippines
SAR/Saudi Arabia
SGD/Singapore
ZAR/South Africa
IDR/Indonesia