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Cheap flight tickets to Chicago

Chicago, a city of stunning skyscrapers and endless energy, has a story to tell on every block. Whether you are gazing up at architectural marvels, exploring the vibrant energy of Millennium Park, or savoring a slice of legendary deep-dish pizza, you'll feel the city's vibrant pulse. Taking flights to Chicago is your ticket to an unforgettable American adventure in one of the nation's most dynamic hubs.

Instantly find and book cheap flights to Chicago (CHI) from hundreds of top airlines. Our powerful search engine scans thousands of real-time fares to bring you the best deals on flight tickets to both O'Hare (ORD) and Midway (MDW). Whether you're planning a family vacation, a business trip, or a last-minute getaway, your search for the lowest price ends here.

Cheap Flights to Chicago (CHI): Pro Tips

  • Cheapest Time to Fly: Winter (Jan-Mar). For the best mix of weather and value, aim for shoulder seasons (Apr-May & Sep-Oct).
  • Best Time to Book: Secure the lowest prices by booking your domestic flight 1-3 months in advance.
  • Airport Savings Hack: Always compare O'Hare (ORD) vs. Midway (MDW). MDW is often cheaper for budget domestic flights.

Chicago is served by major airlines including Qatar Airways, Spirit Airlines, Frontier Airlines, Qatar Airways, ITA Airways, KLM Airlines, Lot Polish Airlines, TAP Air Portugal Airlines, Lufthansa, Scandinavian Airlines, Southwest Airlines, Turkish Airlines, United Airlines offering travelers convenient and affordable flight options.

Explore popular routes

United Airlines

Turkish Airlines

Lot Polish Airlines

Qatar Airways

Qatar Airways

Lufthansa

Scandinavian Airlines

Unlock up to 30% off on your Chicago flight and travel for less.

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Airports in Chicago

  • CHI - CHI - Chicago All Airports, Illinois, United States
  • GYY - Gary Regional
  • MDW - Midway
  • ORD - Ohare International

Top tips for finding a cheap flight to Chicago

Be Flexible with Your Travel Dates

The single biggest way to save is to be flexible. Flying on a Tuesday or Wednesday is often much cheaper than on a Friday or Sunday. Early morning or late-night flights also tend to have lower prices. Use our flexible date search to compare fares across a whole week or month.

Consider Nearby Airports

If your destination has multiple airports, compare the costs of flying into each. You might find that landing at a smaller, nearby airport and taking a short bus or train ride to your final destination saves you a significant amount.

One-Way Tickets Might Be Cheaper

Booking two one-way tickets on different airlines can often be cheaper than a single round-trip ticket. Our search engine automatically compares these options to find you the best possible combination.

Consider Flights with Layovers

If you’re not in a hurry, choosing a flight with a longer layover can drastically reduce the price. Some cities even offer free city tours for travelers on extended layovers, giving you a bonus mini adventure.

Book Flights Separately

Booking separate legs of a journey with different airlines can often save you money. Rather than relying on a single airline for a round-trip or multi-stop ticket, mixing airlines can yield cheaper fares.

Best time to book cheap flights to Chicago

Book your Chicago flight 1-3 months out for the lowest prices, especially if you plan to travel during the popular summer season. The cheapest rates are found during the winter off-season (Jan-Mar), while the shoulder seasons (Apr-May, Sep-Oct) offer the best overall value. For an extra discount, always try to fly mid-week.

  • Be flexible with your dates

    Weekdays and off-peak seasons often offer lower fares. Consider traveling during the shoulder seasons (spring or fall) to avoid peak tourist times.

  • Book in advance

    Generally, booking your flights for Chicago well in advance can lead to better prices. Airlines often release their cheapest fares several months before departure.

  • Consider alternative airports

    If you're flexible about your destination, exploring nearby airports might reveal significant savings. Sometimes, flying into a smaller airport can be more affordable.

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FAQs- booking flights

Finding cheap flights to Chicago requires flexibility and research. Consider booking in advance, using price comparison tools, and being flexible with your travel dates. Additionally, setting price alerts on travel websites can help you track deals and promotional fares.

The best time to visit Chicago depends on what you’re looking for in your trip. Typically, shoulder seasons—spring and fall—offer pleasant weather and fewer crowds. However, visiting during off-peak seasons can help you find cheaper flights and accommodations.

Flight times to Chicago will vary based on your departure location. For example, from the U.S. East Coast, flights might take 7-8 hours, whereas flights from Europe could be 6-9 hours, depending on the city. Check your specific route for more details.

Tuesdays and Wednesdays are often the cheapest days to book flights to Chicago, as demand is typically lower. Prices tend to be higher on weekends when more people are looking to travel.

The cheapest months to book flights are usually during the low season, which often falls in January, February, and September for many popular travel destinations. Avoid peak tourist months like July and December for the best prices.

Low-cost carriers often provide the cheapest flights to Chicago, but it depends on your departure location. Airlines such as Ryanair, Southwest, EasyJet, or JetBlue are known for budget-friendly fares. However, always compare multiple airlines to find the best deal.

The low season for booking cheap flights to most destinations falls in winter (excluding holiday periods) and late summer to early fall. During these times, fewer people are traveling, leading to lower ticket prices.

The high season for flights typically coincides with major holidays, school vacations, and summer months. Expect higher prices from June to August and during December for most destinations worldwide.

Low-cost airlines like Spirit, Frontier, and Norwegian often provide some of the cheapest flights to many cities. Depending on the route, larger carriers like American Airlines, Delta, or Lufthansa may also offer competitive prices during sales.

The average price for a round-trip flight to Chicago can vary based on your departure city, time of booking, and season. On average, you can expect to pay anywhere from $300 to $800, though prices can be lower or higher depending on the factors mentioned.

It depends on the airline, but Midway (MDW) is often cheaper for domestic flights, as it is a major hub for budget-friendly Southwest Airlines. O'Hare (ORD) is a massive international hub with more airline choices, which can sometimes lead to competitive sales, but always compare both to find the best deal.

Flying on a Tuesday or Wednesday is almost always the cheapest option for traveling to Chicago. Flights on Fridays and Sundays are the most popular and, therefore, the most expensive.
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