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Cheap flights to Chicago

Compare every airline flying into Chicago, IL, USA and get phone-only deals you won't see on Google Flights.

Chicago, IL, USA· Airport: ORD
Chicago — Flights | CheapoTrav travel guide

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Key facts

  • Chicago is served by two major airports: O'Hare International (ORD) and Midway International (MDW).
  • MDW is generally closer to downtown Chicago, often preferred by budget airlines and travelers seeking shorter commutes.
  • Book domestic flights to Chicago 6-10 weeks out; for international, aim for 3-6 months in advance for better rates.
  • Midweek flights, specifically Tuesdays and Wednesdays, often offer lower fares compared to peak travel days.
  • Consider flying during the shoulder seasons (late spring, early fall) to avoid peak summer prices and crowds.
  • Direct flights are common, but connecting flights through smaller hubs can sometimes yield additional savings.
  • Chicago's public transit (CTA 'L' trains) offers direct connections from both O'Hare and Midway airports to downtown.

Finding affordable airfare to Chicago requires a bit of savvy, but it's entirely achievable. The city is a major hub, served by two primary airports: O'Hare International (ORD) and Midway International (MDW). O'Hare, one of the world's busiest airports, handles a vast number of domestic and international flights, often offering more options but sometimes longer travel times from the city center. Midway, while smaller, is closer to downtown and a common choice for budget carriers, potentially providing quicker access to your final destination.

When planning your trip, consider the time of year. Summer and the holiday season generally see higher demand and subsequently higher prices. For better deals, look into shoulder seasons — late spring (April-May) or early fall (September-October) — when the weather is pleasant and tourism isn't at its peak. Tuesdays, Wednesdays, and Saturdays are often the sweet spots for booking and flying, as these days typically have lower passenger traffic compared to weekends or Mondays and Fridays.

Flexibility with your travel dates can be your most powerful tool. Even shifting your departure or return by a day or two can sometimes unlock significantly cheaper fares. Look at flights landing at either Midway or O'Hare; don't limit your search to just one, as the competition between the two can drive prices down. Also, consider connecting flights through smaller regional airports if direct flights are proving too expensive, though weigh the savings against the increased travel time and potential for delays.

Keep an eye on fare sales and set price alerts. Many airlines run promotions throughout the year. Subscribing to newsletters from major carriers that fly to Chicago can keep you informed. For those harder-to-find deals or complex itineraries, especially if you're traveling internationally or with specific requirements, speaking directly with a travel agent might uncover options not readily visible online.

In this guide

  • Average flight prices to Chicago
  • Best time to book
  • Direct flights and routing options
  • Tips for cheaper fares

Frequently asked questions

Which airport should I fly into when visiting Chicago?
Chicago has two main airports: O'Hare International (ORD) and Midway International (MDW). O'Hare is larger and serves more airlines, including many international routes, but is further from downtown. Midway is smaller, often served by budget carriers like Southwest, and significantly closer to the Loop. Your choice depends on your starting point, airline preference, and how quickly you want to reach your final destination in the city. Factor in transit time and cost from each airport when deciding.
What's the best time of year to find cheap flights to Chicago?
Generally, the cheapest flights to Chicago can be found outside of peak tourist seasons. Late fall (November, excluding Thanksgiving) and winter (January-March, excluding holidays) often present the lowest fares due to colder weather. The shoulder seasons, such as late April through May and September through October, can also offer good deals with more pleasant weather, though prices will likely be higher than in deep winter. Avoid summer (June-August) and major holidays if budget is your primary concern.
Call 1 (815) 473-8090 for phone-only fares
How far in advance should I book my flight to Chicago?
For domestic flights to Chicago, aim to book between 6 to 10 weeks before your intended travel date. If you're flying internationally, expanding that window to 3 to 6 months in advance can significantly improve your chances of securing a better price. Flexibility is key; adjusting your travel dates by even a day or two can sometimes reveal more affordable options, especially if you can fly on a Tuesday or Wednesday.
Are there budget airlines that fly into Chicago?
Yes, several budget airlines serve Chicago. Southwest Airlines is a major presence at Midway International Airport (MDW), offering numerous routes. Other low-cost carriers like Spirit Airlines, Frontier Airlines, and Allegiant Air also operate flights to both O'Hare (ORD) and Midway, depending on their route networks. Comparing fares across these carriers, and checking both airports, is a good strategy for finding competitive prices.
Call 1 (815) 473-8090 for phone-only fares
Can I get a direct train from Chicago's airports to downtown?
Yes, both O'Hare (ORD) and Midway (MDW) airports are directly connected to downtown Chicago via the CTA 'L' train system. From O'Hare, take the Blue Line directly into the Loop. From Midway, the Orange Line provides direct service to downtown. This public transit option is generally the most cost-effective way to get to and from the airports, offering a reliable alternative to taxis or rideshares, especially during heavy traffic.
What factors influence flight prices to Chicago the most?
Several factors heavily influence flight prices to Chicago. Primary among them are demand (peak seasons like summer or holidays drive prices up), the timing of your booking (earlier generally means better deals), flexibility with travel dates (midweek flights are often cheaper), and the day of the week you search for fares. Airline competition on specific routes and fuel costs also play a role. Being adaptable and monitoring prices are effective strategies for finding lower fares.
Call 1 (815) 473-8090 for phone-only fares

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