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$36 Cheap Flights to Glenwood, IL

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Popular airlines to Glenwood

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How much is the cheapest flight to Glenwood?

Prices were available within the past 7 days and start at $36 for one-way flights and $75 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Frontier Airlines
Frontier Airlines
Southwest Airlines
Delta

Alternative airports near Glenwood

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

What you need to know for your flight to Glenwood

Flights to Glenwood at a glance

Traveling to Glenwood is easy—simply choose between full-service and low-cost airlines, compare travel times, and select the option that best fits your budget, schedule, and plans to explore the city's renowned attractions and neighborhoods.

  • Major airports near Glenwood: O'Hare International Airport (ORD), Midway International Airport (MDW)
  • Closest (typical) airport to Glenwood: Midway International Airport, MDW (around 18 miles)
  • Flights per week: 9,800+ flights arriving across Glenwood airports
  • Number of airlines that fly to Glenwood: around 75+ carriers

Popular airports near Glenwood

Glenwood is a lively city perfect for family outings, outdoor adventures, and sports vacations. Visitors flock here for a mix of family-friendly activities, sports, business opportunities, and city experiences. The city is conveniently accessible through two major airports.

  • O'Hare International Airport (ORD): Situated in Cook County, Illinois, approximately 34 miles from Glenwood, this airport offers a wide array of domestic and international flights, linking travelers to over 285 domestic cities and more than 315 international locations. Passengers can opt for upgrades to first class, premium economy, or business class seating for enhanced comfort, based on their chosen routes and airlines. Notable carriers operating here include American Airlines, United, and Frontier Airlines.
  • Midway International Airport (MDW): Located in Cook County, Illinois, just about 18 miles from Glenwood, this airport provides both domestic and international flight options, serving approximately 130 domestic cities and around 30 international destinations. Travelers can upgrade to premium economy or first class seating for a more comfortable experience, depending on their selected routes and airlines. Leading airlines at this airport include Southwest Airlines, Frontier Airlines, and Delta.

Top routes to Glenwood

  • New York (JFK/LGA) to Glenwood (ORD/MDW), with one-way flight options from around $45
  • Los Angeles (LAX) to Glenwood (ORD/MDW), with one-way fares starting at around $80
  • Boston (BOS) to Glenwood (ORD/MDW), with one-way tickets available from around $50
  • Orlando (MCO) to Glenwood (ORD/MDW), with one-way fares starting at around $45
  • Atlanta (ATL) to Glenwood (ORD/MDW), with one-way flights starting at around $40

Cheapest routes to Glenwood

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

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

Top airlines with flights to Glenwood

  • American Airlines: Operating flights to O'Hare International Airport (ORD), American Airlines accounts for roughly 31% of the arrivals in Glenwood. The typical one-way fare is around $390, with options for premium economy, business, and first-class service depending on the itinerary.
  • United: Also servicing O'Hare International Airport (ORD), United makes up about 31% of Glenwood's incoming flights. Passengers can expect an average one-way fare of approximately $380, and there are premium options like premium economy, business, and first class based on the route.
  • Southwest Airlines: Providing access to both O'Hare International Airport (ORD) and Midway International Airport (MDW), Southwest Airlines accounts for about 12% of arrivals in Glenwood. The average one-way fare is approximately $220, making it an affordable choice for travelers.
  • Delta: With flights to both O'Hare International Airport (ORD) and Midway International Airport (MDW), Delta represents around 8% of Glenwood's flight arrivals. The average fare for a one-way ticket is approximately $290, with premium economy, business, and first class available based on the route.
  • Frontier Airlines: Serving O'Hare International Airport (ORD) and Midway International Airport (MDW), Frontier Airlines contributes about 4% of all arrivals to Glenwood. The average one-way fare is around $160, making it a budget-friendly option for many travelers.

Best time to fly to Glenwood

The most popular months for travelers to fly to Glenwood are January, March, and April, when peak temperatures in Glenwood can reach up to 48.7°F in April. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 66.9°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
February27.0°F (-2.8°C)Light RainMostly CloudyAverage$217
March39.0°F (3.9°C)Light RainMostly CloudyModerately High$242
April48.7°F (9.3°C)Light RainMostly SunnyModerately High$232
May60.6°F (15.9°C)Light RainMostly SunnyAverage$214
June70.2°F (21.2°C)Light RainMostly SunnyAverage$226
July74.1°F (23.4°C)Light RainMostly SunnyAverage$223
August73.0°F (22.8°C)Light RainMostly SunnyAverage$215
September66.9°F (19.4°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
December32.0°F (0.0°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 Glenwood

Getting some of the best deals on flights to Glenwood 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.*
  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 Glenwood flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Glenwood

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

  • Public transportation: From O'Hare International Airport, O'Hare Station, a metro station, is just a 0.1-mile walk away, while Rosemont Station, a train station, is located about 2.2 miles from the airport and typically reached by car.
  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Glenwood, with private rides that can be arranged in advance.
  • Car rental: Renting a car in Glenwood is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Glenwood 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 around Glenwood

  • Lansing: Lansing, located 4 miles away from Glenwood, is a vibrant city perfect for family outings and outdoor adventures. Visitors can enjoy a range of activities, from exploring the Griffin Museum of Science and Industry to relaxing at Centennial Park, an urban oasis ideal for picnics and leisurely strolls. For those interested in culture, Purdue University Northwest offers a glimpse into academic life, while the local shopping center provides a great spot for retail therapy. Lansing's blend of recreational areas and entertainment venues makes it a delightful destination.
  • Matteson: Situated 8 miles drive away from Glenwood, Matteson is a lively city known for its entertainment and outdoor experiences. Families can enjoy various activities, including concerts and theater shows at local venues. The Griffin Museum of Science and Industry serves as a cultural highlight, while the Tinley Park Convention Center caters to business travelers. Outdoor enthusiasts can unwind at the urban parks or challenge themselves at Ravisloe Country Club, making Matteson a versatile choice for visitors seeking both fun and relaxation.
  • Harvey: Located 5 miles away from Glenwood, Harvey offers an engaging mix of family-friendly activities and cultural experiences. The city features venues for theater and music concerts that cater to diverse tastes. Key attractions like the Griffin Museum of Science and Industry provide educational fun, while the Harvey Community Center and Public Library are excellent stops for those interested in local culture. With its inviting parks and sports facilities, Harvey is a great destination for families looking to explore and enjoy the outdoors.

Tips for short-haul flights to Glenwood

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, it's often more economical to travel with just a carry-on. Maximize space by opting for mini toiletries, wearing your bulkiest clothing, and planning your outfits wisely. This strategy also helps you avoid the wait at baggage claim upon arrival.
  • Bring your own entertainment—many short-haul flights might lack in-flight entertainment options. To keep yourself entertained, download TV shows, movies, music, or podcasts beforehand, and consider bringing a book. Remember to fully charge your devices before you board.
  • Arrive at the airport in plenty of time—even for short or domestic flights, it's advisable to arrive 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 carry a refillable water bottle to stay hydrated and save money at the airport.

Tips for long-haul flights to Glenwood

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

  • Select your seat in advance—for longer flights, choosing your seat is essential for comfort. Full-service airlines often provide complimentary seat selection once online check-in opens, typically 24–48 hours before your flight. Some airlines may allow seat selection even earlier.
  • Arrive at the airport in plenty of time—aim to arrive at the airport at least 3 hours before your departure for international flights to accommodate check-in, security, and immigration procedures.
  • Relax at the airport—if you have some extra time, consider browsing the shops, visiting a coffee shop, or unwinding at the gate or in a departure lounge if you have access. Most airports offer free and accessible Wi-Fi.
  • Adjust to the new time zone mid-flight—begin aligning your body clock by changing your watch and adjusting your sleep schedule to correspond with your destination's time zone. Try to sleep or stay awake during the flight according to the local time of your arrival destination to minimize jet lag.

Frequently asked questions

What month is the cheapest to fly to Glenwood?
The cheapest month to fly to Glenwood is August when demand is low. Off-peak months are typically when you'll find cheap flights. To save money, avoid flying during public holidays and school breaks.
Which US cities have the cheapest flights to Glenwood?
Score cheap flights to Glenwood from New York, Washington and Dallas. These cities typically offer the lowest fares to this exciting destination. But remember that demand, seasonality and stopovers will also have an impact on rates, so stay flexible and book when you see a bargain.
Which US cities fly direct to Glenwood?
You can fly to Glenwood without any stops from 150 US destinations. To find a nonstop route, use the "Direct flights only" filter when looking for flights to Glenwood on Expedia. Then, explore your options and find the best departure from one of these cities:
  • New York
  • Washington
  • Dallas
  • Boston
  • Phoenix
How to find a cheap flight to Glenwood?
Traveling in the low season and booking ahead of time are two easy ways to get cheap flights to Glenwood. Or, consider departing on a Thursday, which, on average, is 16% cheaper than leaving on a Sunday.* Want to be the first to know when fares drop? Just set up price tracking on the Expedia app for real-time updates.*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 Glenwood?
You can find awesome deals on last-minute flights to Glenwood, especially if your travel arrangements are flexible. Consider your options for departing from a different airport, changing your dates or picking an alternative airline to get a cheap flight to Glenwood.
How far in advance should I book a flight to Glenwood?
Lock in your flight to Glenwood two to four months ahead if you're jetting in from an international destination. For domestic travel, the usual timeframe is 28 days in advance. Better deals and a wider variety of travel dates, schedules and seating options are just some of the advantages of booking early.**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 Glenwood?
Sundays are generally the best day to book a cheap flight to Glenwood, with savings of about 8% on average compared to a Friday. If you purchase tickets on a Friday, expect to pay a higher price as this is often the most expensive day.**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 Glenwood?
You'll find two popular airlines that travel to Glenwood. Pack your bags and jet off with either of these:
  • United Airlines - 13,395 flights to Glenwood each month, including 13,391 flights to O'Hare Intl. Airport (ORD) per month.
  • American Airlines - 10,417 flights to Glenwood each month, including 10,417 flights to O'Hare Intl. Airport (ORD) per month.
Where do you fly into Glenwood?
If you're flying to Glenwood, the main airport to land at is Midway Intl. Airport (MDW). You can also head for nearby hubs like Lewis University Airport (LOT), O'Hare Intl. Airport (ORD) or Gary, IN (GYY-Gary - Chicago Intl.). Another great option worth keeping in mind when you fly to Glenwood is Joliet Park District Airport (JOT).
Can I save money by booking a Glenwood trip package?
Book a Glenwood flight and hotel package deal on Expedia, and you can make significant savings. It's a breeze to bundle your accommodations and flights, and you can add car rentals and activities to create your own customized Glenwood trip. Plus, there's nothing like the convenience of booking everything in the same place.
Can I change or cancel my flight to Glenwood?
You can often cancel or change your flight to Glenwood within 24 hours of booking. However, be mindful that some flights are non-refundable. In those cases, you may be issued a credit toward a future trip in place of a direct refund. Remember to check the airline's terms of service in your itinerary for specific details. Use Expedia's "Changes included" or "No cancel fee" filters during your search to find cheap flights to Glenwood with flexible change policies. To learn more, browse our Customer Service Portal.

*Flight schedules are subject to change.

*Available to One Key members.

Book with confidence

Tips to find the cheapest flights to Glenwood

The cheapest day to fly

Get started finding a cheap flight to Glenwood 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

August is the cheapest month to fly to Glenwood. 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 Glenwood. 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 Glenwood, 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 Glenwood

The lowest price for round-trip flights to Glenwood in 2026 starts from from $75, while one-way tickets start from from $36. 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 Glenwood. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Glenwood

Frontier Airlines, Southwest Airlines, Delta are just some of the airlines that can typically offer cheap tickets to Glenwood. 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 Glenwood and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Glenwood, 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 Glenwood. 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 Glenwood 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 Glenwood

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 Glenwood.

Stopover savings

The cheapest tickets to Glenwood are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Glenwood. 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 Glenwood 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 Glenwood. Simply download the free Expedia app to your smart device and activate Glenwood 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 Glenwood. 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.

Tips to find the cheapest flights to Glenwood

Travel information

Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Roundtrip price
$75

Trending flights to Glenwood

Prices were available within the past 7 days and start at $36 for one-way flights and $75 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines

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