Cheap Flights to Crestwood, IL

Popular airlines to Crestwood

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Alternative airports near Crestwood

Prices were available within the past 7 days. Prices and availability are subject to change.

What you need to know for your flight to Crestwood

Flights to Crestwood at a glance

Traveling to Crestwood is easy; you can choose between full-service or budget airlines. Compare flight durations and select the option that best fits your budget, schedule, and plans to explore the city's renowned attractions and neighborhoods.

  • Major airports near Crestwood: O'Hare International Airport (ORD), Midway International Airport (MDW)
  • Closest airport to Crestwood: Midway International Airport, MDW (around 9 miles)
  • Flights per week: 9,800+ flights arriving across Crestwood airports
  • Number of airlines that fly to Crestwood: around 75+ carriers

Popular airports near Crestwood

Crestwood is a vibrant city ideal for family getaways, city explorations, and business trips. Visitors are drawn to Crestwood for its outdoor activities, family-friendly attractions, sports events, and cultural experiences. The city is conveniently accessible via two major airports.

  • O'Hare International Airport (ORD): Situated in Cook County, Illinois, approximately 23 miles from Crestwood, O'Hare is a major hub for both domestic and international flights. It connects to over 285 domestic cities and more than 315 international locations. Travelers can opt for premium seating options such as first class, premium economy, and business class, depending on their chosen airline and route. Notable carriers at this airport include American Airlines, United, and Frontier Airlines.
  • Midway International Airport (MDW): Found in Cook County, Illinois, about 9 miles from Crestwood, Midway caters to both domestic and international travelers. It links to around 130 domestic cities and 30 international destinations. Passengers can enhance their travel experience by selecting premium economy or first class seating based on the airline and flight path. Popular airlines operating from Midway include Southwest Airlines, Frontier Airlines, and Delta.

Top routes to Crestwood

  • New York (JFK/LGA) to Crestwood (ORD/MDW), with one-way airfare from around $45
  • Los Angeles (LAX) to Crestwood (ORD/MDW), with one-way flight options from around $80
  • Boston (BOS) to Crestwood (ORD/MDW), with one-way flight options from around $50
  • Orlando (MCO) to Crestwood (ORD/MDW), with one-way airfare from around $45
  • Atlanta (ATL) to Crestwood (ORD/MDW), with one-way airfare from around $40

Cheapest routes to Crestwood

  • Newark (EWR) to Crestwood (ORD/MDW), with affordable one-way prices from around $30
  • Dallas (DFW/DAL) to Crestwood (ORD/MDW), with low one-way fares from around $35
  • Atlanta (ATL) to Crestwood (ORD/MDW), with low-cost one-way tickets from around $40
  • Minneapolis (MSP) to Crestwood (ORD/MDW), with affordable one-way prices from around $40
  • Nashville (BNA) to Crestwood (ORD/MDW), with affordable one-way prices from around $40

*Flight times and fares vary by season and availability and are based on one-way routes

Top airlines with flights to Crestwood

  • American Airlines: Operating flights to O'Hare International Airport (ORD), this airline comprises about 31% of arrivals in Crestwood. The typical one-way fare hovers around $390, with premium cabin services including premium economy, business, and first class depending on the specific route.
  • United: Also servicing O'Hare International Airport (ORD), United Airlines accounts for roughly 31% of Crestwood's arrivals. Travelers can expect an average one-way fare of about $380, with options for premium economy, business, and first-class service based on the route.
  • Southwest Airlines: This airline operates flights to both O'Hare International Airport (ORD) and Midway International Airport (MDW), making up around 12% of arrivals to Crestwood. The average one-way fare is approximately $220, making it a budget-friendly choice.
  • Delta: Providing flights to both O'Hare International Airport (ORD) and Midway International Airport (MDW), Delta represents about 8% of arrivals in Crestwood. The average one-way fare is around $290, with premium cabin options like premium economy, business, and first class varying by route.
  • Frontier Airlines: Operating to both O'Hare International Airport (ORD) and Midway International Airport (MDW), Frontier Airlines accounts for roughly 4% of arrivals to Crestwood. With an average one-way fare of about $160, it is an economical travel option.

Best time to fly to Crestwood

The most popular months for travelers to fly to Crestwood are January, March, and April, when peak temperatures in Crestwood can reach up to 48.2°F in April. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 67.1°F and typically the lowest average one-way fare (around $200), roughly 10% cheaper than the yearly average. Looking for additional cheaper months to fly? October, November, and May offer average one-way fares roughly ranging from $201 to $214, making them good options for flexible travelers.

calendar iconMonthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinesscrowd level iconDemandprice iconAverage one-way Fare
January25.0°F (-3.9°C)Light RainMostly CloudyModerately High$275
February26.8°F (-2.9°C)Light RainMostly CloudyAverage$217
March38.7°F (3.7°C)Light RainMostly CloudyModerately High$242
April48.2°F (9.0°C)Light RainMostly SunnyModerately High$232
May59.9°F (15.5°C)Light RainMostly SunnyAverage$214
June69.6°F (20.9°C)Light RainMostly SunnyAverage$226
July74.1°F (23.4°C)Light RainMostly SunnyAverage$223
August73.2°F (22.9°C)Light RainMostly SunnyAverage$215
September67.1°F (19.5°C)Light RainMostly SunnyModerately Low$200
October54.7°F (12.6°C)Light RainMostly SunnyAverage$201
November41.7°F (5.4°C)Light RainMostly SunnyModerately Low$212
December32.4°F (0.2°C)Light RainMostly CloudyModerately Low$218

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

How to save money on a flight to Crestwood

Getting some of the best deals on flights to Crestwood is all about timing and flexibility. Here are some key tips to help you save:

  1. Compare flight options—use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  2. Set up price alerts—as an Expedia member you can use Price Tracking to receive notifications when flight prices change.
  3. Bundle and save—book a flight and unlock a hotel deal on Expedia*, or explore our Crestwood hotel and flight deals.
  4. Think about luggage-nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your baggage allowance before confirming your booking to avoid excess baggage fees at the airport.
  5. Earn miles—you can earn airline miles when you book your Crestwood flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Crestwood

Crestwood welcomes travelers through its range of transport options based on price, convenience, and proximity. Here's how to reach Crestwood efficiently:

  • Public transportation: From O'Hare International Airport, O'Hare Station, a metro station, is located about 0.1 miles away by walking, while Rosemont Station, a train station, is approximately 2.2 miles from the airport and is best reached by car.
  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Crestwood, with private rides that can be arranged in advance.
  • Car rental: Renting a car in Crestwood is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Crestwood on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.

Where to stay in and around Crestwood

  • Chicago: As a vibrant metropolis, Chicago offers a wealth of experiences that cater to families, outdoor enthusiasts, and city explorers alike. Crestwood is situated in Chicago, providing easy access to a variety of attractions like the stunning Griffin Museum of Science and Industry, perfect for cultural outings with the family. Visitors can also enjoy the iconic 875 North Michigan Avenue skyscraper and the bustling Michigan Avenue, known for its shopping and entertainment options. Don't miss the local sports facilities and urban parks that enhance the city's charm.
  • Homer Glen: Located 10 miles away from Crestwood, Homer Glen is an inviting city ideal for families and outdoor lovers. The area boasts picturesque urban parks and a vibrant arts scene, making it a great spot for entertainment. Key highlights include the Tinley Park Convention Center, which hosts various events, and the historic Lewis University, offering a glimpse into the local culture. For nature enthusiasts, the Morton Arboretum presents a beautiful escape filled with lush landscapes and educational opportunities.
  • Matteson: Situated 11 miles drive away from Crestwood, Matteson is a dynamic city that offers something for everyone, from family-friendly activities to outdoor adventures. Visitors can explore vibrant theaters and enjoy live music concerts. Notable destinations include the Griffin Museum of Science and Industry and the Tinley Park Convention Center, both excellent venues for culture and events. The Ravisloe Country Club also provides a scenic golf experience, making Matteson an appealing choice for leisure and recreation.

Tips for short-haul flights to Crestwood

For quick getaways, efficiency is key. Here is how to make your short-haul journey smoother:

  • Pack light and skip checked bags—when flying with budget airlines, traveling with just a carry-on is often more economical. Maximize space by using mini toiletries, wearing your bulkiest clothing, and planning your outfits wisely. This approach also lets you avoid the wait at baggage claim upon arrival.
  • Bring your own entertainment—many short-haul flights might not provide in-flight entertainment. To keep yourself occupied, download TV shows, movies, music, or podcasts ahead of time, and consider bringing a book. Be sure to charge your devices fully before you board.
  • Arrive at the airport in plenty of time—even for short or domestic flights, it's advisable to get to the airport at least 1.5 to 2 hours prior to departure, taking into account traffic and security lines.
  • Bring your own snacks and water—pack some snacks and a refillable water bottle to stay hydrated and save money while at the airport.

Tips for long-haul flights to Crestwood

Flying long-haul sometimes requires extra planning to ensure a comfortable journey:

  • Select your seat in advance—for longer flights, choosing your seat is crucial for comfort. Full-service airlines often allow free seat selection once online check-in opens, typically 24–48 hours before your flight. Some airlines may provide the option to select seats even earlier.
  • Arrive at the airport in plenty of time—make sure to arrive at the airport at least 3 hours prior to departure for international flights to allow sufficient time for check-in, security, and immigration.
  • Relax at the airport—if you have some extra time, take the opportunity to browse the shops, find a coffee shop, or unwind at the gate or in a departure lounge if you have access. Most airports offer free Wi-Fi for your convenience.
  • Adjust to the new time zone mid-flight—begin to sync your body clock by changing your watch and sleep schedule to align with your destination's time zone. Try to sleep or stay awake on the flight according to the local time at your arrival destination to help minimize jet lag.

Frequently asked questions

What month is the cheapest to fly to Crestwood?
The cheapest month to fly to Crestwood is when there's less demand. Off-peak months are typically when you'll find cheap flights. To save money, avoid flying during public and school holidays.
Which US cities have the cheapest flights to Crestwood?
Score cheap flights to Crestwood from New York, Washington and Dallas. These cities generally offer the best fares to this exciting destination. But bear in mind that holiday periods, stopovers and demand will also impact rates, so remain flexible and book when you see a bargain.
Which US cities fly direct to Crestwood?
You can fly to Crestwood without any stops from 150 US cities. To find a nonstop trip, use the "Direct flights only" filter when looking for flights to Crestwood on Expedia. Then, explore the options and pick the best departure out of one of these cities:

  • New York
  • Washington
  • Dallas
  • Boston
  • Phoenix

How to find a cheap flight to Crestwood?
Book in advance to increase your chances of finding cheap flights to Crestwood. Also, consider traveling during off-peak months like January and February. If you fly on a Thursday, you'll save an average of 16% compared to departing on a Sunday.* Save time checking every day and create a price alert on the Expedia app. We'll send you a notification when fares change.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Crestwood?
While booking in advance is usually the easiest way to save cash, don't panic if your Crestwood trip is last minute. You can still get cheap flights to Crestwood, especially if your plans have some flexibility. Try switching up your travel dates, looking at different ticket options or flying out of an alternative hub.
How far in advance should I book a flight to Crestwood?
Get the departure dates you want and a fare that works with your budget by booking your domestic flight to Crestwood up to 28 days in advance. Lock in tickets two to four months ahead if you're traveling to Crestwood from an international destination.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Crestwood?
You can usually find cheap flights to Crestwood on Sundays. You can save around 8% on average compared to those who book on a Friday, which is often the most expensive day to purchase tickets.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Crestwood?
A total of 44 airlines connect 216 airports around the world to Crestwood. Here are some of the major airlines to Crestwood, where O'Hare Intl. Airport (ORD) is the major entry point:

  • United Airlines
  • American Airlines
  • Delta Air Lines
  • Alaska Airlines

Where do you fly into Crestwood?
The main airport when you fly to Crestwood is Midway Intl. Airport (MDW), but there are some good nearby alternatives like Lewis University Airport (LOT) and O'Hare Intl. Airport (ORD). You can also arrive at Gary, IN (GYY-Gary - Chicago Intl.) and Joliet Park District Airport (JOT) when flying to Crestwood.
How far is the airport from central Crestwood?
If you're arriving at Midway Intl. Airport (MDW), you'll be roughly 9 mi north of central Crestwood.
Can I save money by booking a Crestwood trip package?
Book a Crestwood flight and hotel package deal on Expedia, and you could make significant savings. It's a breeze to bundle your hotel and flight, and you can even add car rentals and activities to create your own customized Crestwood trip. Plus, there's nothing like the convenience of booking everything in one place.
Can I change or cancel my flight to Crestwood?
It's often possible to cancel or change your flight to Crestwood. Many airlines let you cancel your ticket for free within 24 hours of booking. However, some flights are non-refundable, and airlines may issue you a credit toward a future trip instead of a direct refund. To find cheap flights to Crestwood with flexible change policies, pick the "Changes included" or "No cancel fee" filters when you search. Looking for more information? Check out our Customer Service Portal.

*Flight schedules are subject to change.

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Travel information

Destination airport
Crestwood
Destination airport IATA code
CHI

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