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Book Flights to Chicago at the Best Price

Looking for cheap flights to Chicago (ORD)? CompareWings helps you find and book the lowest airfare by comparing top airlines and travel agencies in one place. Whether you're visiting for the city's architecture, world-class museums, or diverse neighborhoods, you’ll find the best deals to Chicago right here.

Why Visit Chicago?

Chicago is a dynamic city known for its architecture, vibrant arts scene, and diverse culture. From iconic landmarks like the Willis Tower (formerly Sears Tower) to the world-class museums along the Museum Campus, Chicago is an essential destination for travelers who enjoy city life, food, and art. Chicago also offers stunning lakefront views and historic neighborhoods like Wicker Park and Pilsen.

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When’s a Good Time to Book a Flight to Chicago?

What’s the Cheapest Day of the Week to Fly to Chicago?

If you're looking for the best deals, consider booking your flight to Chicago on Tuesday or Wednesday. These days typically have lower fares compared to weekends.

What is the Cheapest Month to Fly to Chicago?

Historically, January and September are the cheapest months to book Chicago. December and February can be more expensive due to holiday travel.

Major Airport in Chicago

Chicago O'Hare International Airport (ORD) is one of the busiest airports in the world, offering a wide range of domestic and international flights. ORD is located 17 miles northwest of downtown Chicago and provides easy access to the city via car, public transit, or airport shuttles.

Tips to Find Cheap Flights to Chicago

  • Set fare alerts on CompareWings to monitor price changes
  • Book 3-4 weeks in advance for the best deals
  • Be flexible with your travel dates — weekdays are often cheaper than weekends
  • Fly during the off-peak season (late fall and early spring) to find lower fares
  • Consider flying into Midway International Airport (MDW) for additional options

Popular Flight Routes to Chicago

  • Flights from New York to Chicago
  • Flights from Los Angeles to Chicago
  • Flights from Dallas to Chicago
  • Flights from Miami to Chicago
  • Flights from Denver to Chicago

Airlines That Fly to Chicago

Chicago O'Hare International Airport is a major hub for multiple airlines, including:

  • American Airlines
  • United Airlines
  • Delta Air Lines
  • Southwest Airlines
  • Spirit Airlines

Travel Tips When Flying into Chicago

  • The "L" (Chicago Transit Authority) trains provide an affordable way to get from the airport to downtown Chicago
  • Consider renting a car if you plan to explore neighborhoods or the surrounding areas
  • Use ride-sharing services like Uber and Lyft for convenient transportation within the city
  • Chicago has an extensive public transit system, including buses and trains

What to See in Chicago

  • Millennium Park — home to the famous Cloud Gate sculpture ("The Bean")
  • Navy Pier — a popular waterfront destination with shops, restaurants, and rides
  • The Art Institute of Chicago — one of the oldest and largest art museums in the U.S.
  • Willis Tower Skydeck — offering stunning views of the city from one of the tallest buildings
  • Lincoln Park Zoo — a free zoo located in the heart of Chicago
  • Magnificent Mile — a world-class shopping district
  • Wrigley Field — home to the Chicago Cubs and a landmark in baseball history
  • Chicago Riverwalk — a scenic pedestrian path along the river with restaurants and bars
  • Museum of Science and Industry — a family-friendly museum with hands-on exhibits

More Than Flights

With CompareWings, you can also explore:

  • Hotels in Chicago for all budgets
  • Car rentals from ORD Airport
  • Full package deals with flights and accommodation
  • Local activity suggestions and travel guides

Related Flight Pages You May Like

  • Flights to Detroit
  • Flights to New York
  • Flights to Los Angeles
  • Flights to Dallas
  • Flights to Miami

Frequently Asked Questions

Flights to Chicago range from $100 to $400, depending on the season and departure city.

The best times to fly to Chicago are during the spring and fall, when the weather is mild and there are fewer tourists.

Chicago O'Hare International Airport is about 17 miles northwest of downtown, and it takes 30-40 minutes by car or 45 minutes via the "L" train.

Yes, Chicago has an extensive public transportation system, including buses, trains, and commuter rails for easy access to the city and surrounding areas.

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