$41 Cheap Flights to Crestwood, IL

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.

*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.

Tips to find the cheapest flights to Crestwood

The cheapest day to fly

Get started finding a cheap flight to Crestwood on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

The cheapest month to fly

September is the cheapest month to fly to Crestwood. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Crestwood. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute.

The most affordable time to book a flight

Typically, a Sunday can be the cheapest time to book a flight to Crestwood, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation.

The cheapest round-trip tickets to Crestwood

The lowest price for round-trip flights to Crestwood in 2026 starts from $97, while one-way tickets start from from $41. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Crestwood. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Crestwood

Frontier Airlines, American Airlines, Southwest Airlines, United, Delta are just some of the airlines that can typically offer cheap tickets to Crestwood. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Crestwood and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Crestwood, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Crestwood. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia.

Save with a package

With Expedia's amazing package deals, you could save hundreds of dollars by booking your Crestwood plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving.

Date flexibility for the cheapest flights to Crestwood

If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Crestwood.

Stopover savings

The cheapest tickets to Crestwood are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Crestwood. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved.

Get Expedia's Price Drop Protection

Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference*. This gives you peace of mind that you're getting one of the cheapest flights to Crestwood for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members.

*Terms apply.

Use our Price Tracking feature

Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Crestwood. Simply download the free Expedia app to your smart device and activate Crestwood flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices.

Book with Expedia

As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Crestwood. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.