How to Find Cheap Flights from Chicago

To find cheap flights from Chicago, consider traveling midweek, particularly on Tuesdays or Wednesdays, when fares are typically lower. Booking well in advance and being flexible with your travel dates can yield better deals. Visit flytravelboard.com to compare and track price drops.

Best Time to Visit Chicago

The best time to visit Chicago is during spring (April-June) and fall (September-October). The weather is pleasant, and you’ll avoid the summer crowds. These seasons are perfect for exploring Chicago’s parks, festivals, and outdoor attractions without the intense heat or cold.

Best Time to Book Flights from Chicago

The ideal time to book flights from Chicago is 6-8 weeks in advance. This window allows you to lock in lower fares before prices rise closer to the departure date. Avoid last-minute bookings, especially during peak travel seasons like summer or major holidays.

Airports in Chicago

Chicago is served by two major airports: O’Hare International Airport (ORD), one of the busiest airports globally, and Midway International Airport (MDW), known for its focus on domestic and budget airlines. Both airports offer convenient access to downtown Chicago and surrounding areas.

About Chicago

Chicago, located on the shores of Lake Michigan, is a bustling metropolis known for its stunning skyline, vibrant arts scene, and deep-dish pizza. As one of the largest cities in the U.S., Chicago is home to world-class museums like the Art Institute of Chicago and iconic landmarks like the Willis Tower and Millennium Park. Whether you’re exploring the city’s architectural marvels or enjoying a performance at The Chicago Theatre, this city offers something for every traveler. Its diverse neighborhoods, rich history, and culinary delights make Chicago a top destination year-round.

Direct Flights from Chicago

Top five airlines offering direct flights from Chicago:

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united airline
southwest
spirit logo

Top Tips for Finding Cheap Flights from Chicago

  1. Fly midweek: Tuesdays and Wednesdays typically have cheaper fares due to lower demand.
  2. Book early: Plan ahead and secure your tickets 6-8 weeks in advance for the best prices.
  3. Use alternate airports: Compare flights from both O’Hare and Midway for potential savings.
  4. Set fare alerts: Use price tracking tools to monitor fare drops and book at the right moment.

Airline Comparison Table

Responsive Table
Airline Avg. Reviews Pros Cons
Delta Airlines 4.5/5 Reliable,
Large network,
Service
Higher cost,
Delays,
Crowded
American Airlines 4.2/5 Frequent flights,
Routes,
Service
Fees,
Delays,
Overbooking
United Airlines 4.3/5 Connectivity,
Rewards,
Long-haul
Pricing,
Delays,
Extra fees
Southwest Airlines 4.4/5 Free bags,
Budget-friendly,
Flexible
No seat selection,
Domestic focus
Spirit Airways 3.8/5 Cheap fares,
Regular routes,
Domestic
Extra fees,
Basic services,
No extras

Detailed Airline Overviews

1. Delta Air Lines from Chicago

Delta operates a wide range of domestic and international flights from Chicago. Known for its reliability, Delta offers a premium flying experience, though fares are typically higher than budget carriers.

  1. Extensive global network
  2. High-quality service
  3. In-flight entertainment

2. American Airlines from Chicago

American Airlines offers a robust network of flights from Chicago, covering both domestic and international destinations. While the service is reliable, fees for checked baggage and seat selection can add up.

  1. Extensive route network
  2. Comfortable seating options
  3. Frequent flight availability

3. United Airlines from Chicago

As a major hub for United Airlines, Chicago offers many direct flights to both national and international destinations. United is popular for its rewards program and long-haul flight options, though it has been criticized for overbooking.

  1. Great rewards program
  2. Wide-reaching global routes
  3. Frequent long-haul options

4.Southwest Airlines from Chicago

Southwest is a top choice for budget travelers flying domestically from Chicago. The airline doesn’t charge for checked bags and offers flexible booking policies, though it lacks assigned seating.

  1. No baggage fees
  2. Budget-friendly fares
  3. Flexible rebooking policies

5. Spirit Airlines from Chicago

Spirit Airlines is a no-frills, low-cost carrier offering domestic flights from Chicago. While its base fares are low, additional fees for services like baggage and seat selection make it less ideal for travelers seeking a more inclusive experience.

  1. Ultra-low fares
  2. Regular domestic routes
  3. Basic service with extra fees

6. JetBlue Airways from Chicago

JetBlue offers affordable fares with great in-flight comfort, including free Wi-Fi and extra legroom. While it flies fewer routes compared to major airlines, it remains a favorite for budget-conscious travelers seeking comfort.

  1. Spacious seating
  2. Free in-flight entertainment
  3. Affordable pricing

7. Alaska Airlines from Chicago

Alaska Airlines is known for its reliable service and affordable fares. It primarily serves domestic routes but offers a top-tier rewards program that’s popular among frequent travelers.

  1. Great customer service
  2. Affordable fares
  3. Strong rewards program

8. Frontier Airlines from Chicago

Frontier is a low-cost carrier known for offering cheap domestic flights from Chicago. While it’s a budget-friendly option, passengers should be prepared for additional fees for services like seat selection and baggage.

  1. Low-cost fares
  2. Budget-friendly for short trips
  3. Extra fees for amenities

9. British Airways from Chicago

British Airways offers direct flights from Chicago to London and other European destinations. Known for its premium in-flight services, British Airways is an excellent choice for international travelers seeking comfort.

  1. Premium in-flight experience
  2. Direct flights to Europe
  3. Higher fares in economy class

10. Air Canada from Chicago

Air Canada offers direct flights to Canadian cities from Chicago. The airline provides comfortable seating and reliable service, making it a good option for North American travelers, though prices may vary.

  1. Comfortable seating
  2. Reliable service
  3. Pricing may vary

Frequently Asked Questions (FAQs)

Chicago is served by O’Hare International Airport (ORD) and Midway International Airport (MDW).

The best time to visit is in spring (April-June) and fall (September-October) when the weather is mild.

Delta, American Airlines, United, Southwest, and Spirit offer direct flights from Chicago.

Book your flights 6-8 weeks in advance for the best prices.

Southwest Airlines and Spirit Airlines are popular choices for budget-conscious travelers.

Yes, O’Hare International Airport (ORD) is a major hub for international flights.

Yes, flying on Tuesdays and Wednesdays typically offers lower fares due to reduced demand.

Delta and Alaska Airlines have highly rated frequent flyer programs.

Yes, red-eye flights are often cheaper due to lower demand.

United Airlines, American Airlines, and British Airways are top choices for international flights.