Cheap Flight Deals to Chicago Chicago is America's great third city
Find the best cheap flight deals to Chicago O’Hare International Airport (ORD). Compare fares, book in seconds, and discover everything Chicago, Illinois has to offer.
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Your Complete Guide to Flying to Chicago, Illinois
Chicago is one of America’s most extraordinary cities — a global metropolis of 2.7 million on the southwestern shore of Lake Michigan, defined by its stunning architecture, world-class museums, legendary food and music scenes, and an irrepressible civic pride. The city rebuilt itself from the Great Fire of 1871 to become the birthplace of the skyscraper, and its architectural legacy is simply unmatched — Frank Lloyd Wright, Louis Sullivan, Mies van der Rohe, and Helmut Jahn all shaped the city’s extraordinary skyline.
From the electric blues clubs of the North Side to the deep-dish pizza perfection of Lou Malnati’s, from the impressionist masterpieces of the Art Institute to the soaring views from the Willis Tower Skydeck, Chicago delivers world-class experiences at every turn. Book cheap flight deals to Chicago (ORD) and discover why this city is endlessly, irresistibly compelling.
The city’s elevated bluffs above the Mississippi offer spectacular river views from Cape Rock Park, while the River Heritage Museum documents the profound role the Mississippi River has played in the city’s identity. Book cheap flight deals to Cape Girardeau (CGI) and discover one of Missouri’s most authentic and overlooked river cities.identity. Book cheap flight deals to Cape Girardeau (CGI) and discover one of Missouri’s most authentic and overlooked river cities.
One of the oldest and largest art museums in the US with an extraordinary collection including Seurat’s A Sunday on La Grande Jatte, Grant Wood’s American Gothic, and one of the finest Impressionist collections outside France.
The Art Institute of Chicago
The definitive Chicago experience — a 90-minute narrated boat tour along the Chicago River offering unparalleled views of the world’s greatest concentration of architectural masterpieces from the water level.
Chicago Architecture River Cruise
Chicago’s magnificent 24.5-acre lakefront park is home to the iconic Bean (Cloud Gate sculpture), Jay Pritzker Pavilion outdoor concert venue, Crown Fountain, and stunning views of the skyline and Lake Michigan.
Millennium Park & Cloud Gate
Ride to the 103rd floor of what was once the world’s tallest building for breathtaking 360-degree views from the legendary glass-floored Ledge boxes extending 4 feet beyond the building’s facade — not for the faint-hearted.
Willis Tower Skydeck
The Friendly Confines — Wrigley Field (opened 1914) is one of America’s most beloved ballparks, with its ivy-covered outfield walls, hand-operated scoreboard, and an atmosphere unlike any other in baseball.
Wrigley Field & the Cubs
Chicago’s culinary identity is built on deep-dish pizza (Lou Malnati’s, Giordano’s, Pequod’s), Chicago-style hot dogs, Italian beef sandwiches, and a world-class restaurant scene featuring some of America’s most innovative chefs.
Deep-Dish Pizza & Chicago Food Scene
Chicago O'Hare International Airport (ORD)
The primary commercial airport serving Chicago, located 17 miles from downtown. IATA code: ORD. Connects primarily through Chicago O’Hare International (ORD).
Location & Getting Around
Chicago is located in Taylor County, West Texas, approximately 180 miles west of Dallas-Fort Worth. Car rentals are available at ORD airport. The city is easily navigable by car with minimal traffic.
Climate & Weather
Chicago has a semi-arid climate with hot summers (avg. 95°F in July) and mild winters. The city receives about 23 inches of rain annually. Spring and fall offer the most pleasant visiting conditions.
Events & Festivals
Major annual events include the Children’s Art & Literacy Festival (June), Western Heritage Classic Rodeo (May), and Holiday in Chicago (December). Plan flights early around festival dates.
Travel Calendar
Best Time to Fly to Chicago
Airfare and weather guide for every month of the year
JAN
Low fares
FEB
Low fares
MAR
Moderate
APR
Moderate
MAY
Moderate
JUN
Peak season
JUL
Peak season
AUG
Peak season
SEP
Moderate
OCT
Moderate
NOV
Low fares
DEC
Moderate
Cheapest fares
Average fares
Peak / expensive
Routes
Popular Routes to Cape Girardeau (CGI)
Compare fares across the most-searched departure cities
| From | To | From Price | Type |
|---|---|---|---|
| New York (JFK) | Chicago (ORD) | from $89* | Round Trip |
| Los Angeles (LAX) | Chicago (ORD) | from $109* | Round Trip |
| Miami (MIA) | Chicago (ORD) | from $99* | Round Trip |
| Dallas (DFW) | Chicago (ORD) | from $99* | Round Trip |
| Atlanta (ATL) | Chicago (ORD) | from $99* | Round Trip |
| Boston (BOS) | Chicago (ORD) | from $109* | Round Trip |
| Denver (DEN) | Chicago (ORD) | from $109* | Round Trip |
| Seattle (SEA) | Chicago (ORD) | from $119* | Round Trip |
Airport Guide
Chicago Regional Airport (ORD)
Everything you need to know about flying into and out of Chicago’s main commercial airport.
IATA Code
ORD
Chicago
Distance to City
17mi
From downtown Chicago
Main Hub Airlines
AA / 9E
American / Endeavor Air
Key Connections
ORD
Chicago O’Hare International hub
Travel Tips
Tips for Finding Cheap Flights to Chicago
Insider strategies to cut your airfare to ORD significantly
01
Book 3–6 Weeks Ahead
For flights to Chicago, booking 3 to 6 weeks before departure typically yields the best fares. Prices usually rise sharply within 2 weeks of departure.
02
Fly on Tuesdays or Wednesdays
Mid-week departures to ORD are consistently 15–25% cheaper than weekend flights. Avoid Friday and Sunday travel for the lowest rates.
03
Consider Connecting via DFW
Most flights to Chicago connect through Chicago O’Hare International (ORD). Booking this connection often unlocks more schedule options and better pricing. Booking a DFW connection often unlocks more schedule options and better pricing compared to nonstop alternatives.
04
Travel in January, February, or September
These are the off-peak months for Chicago air travel. Fares can be 30–40% lower than during the busy summer season.
05
Set Fare Alerts
Sign up for price drop notifications on your preferred Chicago route. Fares fluctuate daily and a well-timed alert can save you $50–$150 per ticket.
06
Use Flexible Date Search
If your travel schedule allows, check fares ±3 days around your ideal dates. A one-day shift in departure can sometimes cut prices dramatically.
Frequently Asked Questions
Cheap flight deals to Chicago (ORD) start from as low as $89 for round-trip tickets. As one of the world's busiest airports and a dual hub for United and American Airlines, Chicago consistently offers some of the most competitive fares in the country from virtually every US city. Midway (MDW) via Southwest is also worth comparing.
Chicago is served by two major airports — O'Hare International Airport (IATA: ORD), located 17 miles northwest of downtown and serving all major carriers, and Midway Airport (IATA: MDW), 10 miles southwest of downtown and primarily serving Southwest Airlines. Both airports offer excellent transit connections to the city.
January, February, and November offer the lowest airfares to Chicago (ORD). Summer (June-August) is peak tourism season with excellent lakefront weather, outdoor festivals, and Cubs and White Sox games. Spring and fall offer moderate fares and pleasant, if variable, weather.
Chicago O'Hare (ORD) is a dual hub for United Airlines and American Airlines, with every major US and international carrier also operating at ORD. Midway (MDW) is Southwest Airlines' largest hub. Between ORD and MDW, Chicago is served by virtually every airline in the US and hundreds of international carriers.
Chicago's exceptionally high flight frequency means competitive fares are often available with just 2-3 weeks' notice. For summer travel, Lollapalooza weekend (August), and holiday periods, book 6-8 weeks ahead. Always compare both ORD and MDW for the lowest total fare to the Chicago area.
Top attractions include the Art Institute of Chicago, Chicago Architecture River Cruise, Millennium Park and Cloud Gate (the Bean), Willis Tower Skydeck, Wrigley Field (Cubs baseball), deep-dish pizza at Lou Malnati's or Giordano's, the Museum of Science and Industry, Lincoln Park Zoo (free), and the stunning Museum Campus on the lakefront.
Yes — Chicago O'Hare (ORD) has nonstop service from virtually every US city and over 100 international destinations. United and American alone operate nonstop ORD flights from over 100 cities. Midway (MDW) adds nonstop Southwest service from an additional 70+ cities, making Chicago one of the best-connected aviation markets in the world.
Popular Destinations
The Most Popular Cities
Explore top flight destinations travelers love — great deals available now.
Las Vegas
LAS · Nevada
New York
JFK · New York
Washington
DCA · D.C.
Chicago
ORD · Illinois
San Francisco
SFO · California
Los Angeles
LAX · California
Orlando
MCO · Florida
Miami
MIA · Florida
Paris
CDG · France
London
LHR · UK
Rome
FCO · Italy
Amsterdam
AMS · Netherlands
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