Cheap Flights to Glenwood: Glenwood Flight Deals

View €58 flight on Mon, 12 Jan 2026Opens in a new window

Popular airlines to Glenwood

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Cheap round-trip flights to Glenwood

Prices were available within the past 7 days and start at €58 for one-way flights and €114 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 8 Jan - Sun, 11 Jan
ATL
Atlanta
MDW
Chicago
€114 Return, found 16 hours ago
€114
Return
found 16 hours ago
Select Delta flight, departing Thu, 8 Jan from Atlanta to Chicago, returning Sun, 11 Jan, priced at €114 found 16 hours ago
Porter Airlines
Thu, 8 Jan - Sun, 11 Jan
YTZ
Toronto
MDW
Chicago
€159 Return, found 18 hours ago
€159
Return
found 18 hours ago
Select Porter Airlines flight, departing Thu, 8 Jan from Toronto to Chicago, returning Sun, 11 Jan, priced at €159 found 18 hours ago
Air Transat
Thu, 8 Jan - Sun, 11 Jan
YTZ
Toronto
MDW
Chicago
€178 Return, found 18 hours ago
€178
Return
found 18 hours ago
Select Air Transat flight, departing Thu, 8 Jan from Toronto to Chicago, returning Sun, 11 Jan, priced at €178 found 18 hours ago
KLM
Wed, 25 Mar - Tue, 31 Mar
DUB
Dublin
MDW
Chicago
€435 Return, found 5 days ago
€435
Return
found 5 days ago
Select KLM flight, departing Wed, 25 Mar from Dublin to Chicago, returning Tue, 31 Mar, priced at €435 found 5 days ago
Air France
Wed, 3 Dec - Tue, 9 Dec
DUB
Dublin
MDW
Chicago
€577 Return, found 4 days ago
€577
Return
found 4 days ago
Select Air France flight, departing Wed, 3 Dec from Dublin to Chicago, returning Tue, 9 Dec, priced at €577 found 4 days ago

Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD)

July is typically the cheapest month to fly

From €67 - €252 per traveller.

Expedia.ie is an online travel company that specialises in securing the best prices for flights to Glenwood. With Expedia you get highly specialised services, combining the best of technology, in-depth knowledge and the best connections in order to offer great deals to Glenwood. Expedia shares your passion for travel and has built the best online travel service that promotes and encourages travel. Whether you are looking for cheap flights to Glenwood, or are just on the lookout for the best flights to Glenwood, you are sure to find the best deals with Expedia.ie.

"One of the many benefits of booking your flights through Expedia is that we are one of the world’s largest online travel agency, which means we use our collective experience and work tirelessly to bring you the best prices. With Expedia you get a user-friendly internet experience and a dedicated customer support service that ensures that everything goes smoothly. The goal of Expedia is to offer premium services at the lowest price, all at one single place. If you wish to save even more try combing a hotel in Glenwood to your flight and create a personalised low cost city break or holiday to your favourite destination. Book early and you could save even more!

If you have an Expedia.ie itinerary number and have a question or concern about your travel plans you can call us on (01) 524 5005 from 8am - 10pm Monday to Friday, and 9am - 10pm at weekends and an Expedia agent will help you.

Frequently asked questions

What is the name of Glenwood's airport?
Glenwood is served by more than one airport, but most people prefer to touch down at O'Hare Intl. Airport (ORD).
What airport is best to fly into Glenwood?
There are two main airports that connect travellers with Glenwood. ORD is about 56 kilometres from the central area, while Midway Intl. Airport (MDW) is approximately 29 kilometres away. After you find a great price and work out where you're staying, you'll have a better idea of which one to head to.
How many airlines fly to Glenwood?
Glenwood is serviced by 51 air carriers from 237 worldwide airports.
Which airlines fly to Glenwood?
Glenwood receives the most flights from United Airlines, American Airlines and Delta with United Airlines being the favourite choice of carrier. New York is the most popular city for passengers to take off from.
How many nonstop flights are there to Glenwood?
Flying to somewhere new is much easier when there aren't any stopovers to slow you down. If you're heading to Glenwood, the good news is that there are approximately 7,564 nonstop flights each week.
Where are the most popular flights to Glenwood departing from?
A large number of flights to Glenwood set off from New York, Washington and Dallas airports.
How long is the flight to Glenwood Airport?
If it's New York you're leaving behind, you'll be in the sky for around 2 hours and 44 minutes before you touchdown in Glenwood. Airport to airport from Washington takes approximately 2 hours and 15 minutes and from Dallas, it's 2 hours and 18 minutes.
How to book the cheapest flight to Glenwood?
We've all come across those lucky jet-setters who somehow pick up extremely cheap fares wherever they go. Want to know how to do it for your Glenwood holiday? Don't wait until the last moment to secure your flight. Don't stop there, though. Do some research and check if there are multiple airports at your destination. Prices often differ depending on which airport you fly into. Be sure to compare fares across air carriers too. Last of all, be ready to secure your seat quickly if you stumble on a real bargain. It might not be available for long! With a bit of knowledge and some luck, the ideal airfare will be yours.
Do you have any tips for my flight to Glenwood?
Wherever you're coming from, flying can be a pleasurable experience if you've prepared well. We've made a list of top travel tips that will help get your Glenwood escape started on the right note. What to pack in your hand luggage:

  • The trick to having a hassle-free flight experience is to be prepared. First up, the essentials: passport, travel docs, cash and daily medications. Next, bring items that'll help keep you entertained, like some electronic gadgets or a good book. It's also wise to bring your chargers, a neck pillow and a pair of earphones. Last but not least, be sure to pop in toiletry items like a toothbrush, lip balm and a fresh set of clothes.

Do not pack the following items in your hand luggage:

  • Put all your full-sized bottles of hair gel and hairspray in your checked baggage. Any liquids or gels in your carry-on bag larger than 3.4 ounces (100 millilitres) will be confiscated. Sharp objects, like your trusty Swiss Army knife, and products which are explosive or flammable, such as spray paint, flares and fireworks, are also prohibited.

What to wear on a flight:

  • Comfort should be your number one priority when choosing what to wear on your flight. Loose clothing is a wise choice, as are flat, slip-on shoes.
  • Deep vein thrombosis (DVT), a blood clot condition caused by lengthy periods of inactivity, can be a risk on long-haul flights. Try to walk around the cabin and stretch your legs or do some gentle exercises in your seat to promote better circulation.

How to get through airport security fast when flying to Glenwood?
As savvy travellers know, the secret is to be organised before you arrive at the airport security gate. That way, you'll be hopping onto that plane to Glenwood in next to no time. Follow these tips and get your holiday off to a spectacular start:

  • Be sure to keep your passport and travel documents close by. They're the first things you'll be asked to show at security.
  • Next up, both you and your hand luggage must be X-rayed. To speed things up, take off anything that is likely to set the alarm off. Personal belongings like your belt, coat and earphones will be required to go through the machine.
  • For just a few moments, you'll have to unplug from technology. Your tablet, phone and any other electronics must also go through the scanner.
  • Any gels or liquids, such as perfume or hand cream, that you want to take on board must be no greater than 3.4 ounces (100 millilitres). They must also all fit inside a quart-size (one litre), clear zip-close bag.
  • Slip-on shoes are a clever footwear choice as you're less likely to be asked to remove them when going through security. Boots and heavier-style shoes are usually subjected to additional screening.
  • Airlines will not allow any sharp objects in your carry-on luggage. If you must bring these kinds of items, put them in your checked luggage.

Flights to Glenwood information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Return price
€114

Trending flights to Glenwood

Prices were available within the past 7 days and start at €58 for one-way flights and €114 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

KLM
Wed, 25 Mar - Tue, 31 Mar
DUB
Dublin
MDW
Chicago
€435 Return, found 5 days ago
€435
Return
found 5 days ago
Select KLM flight, departing Wed, 25 Mar from Dublin to Chicago, returning Tue, 31 Mar, priced at €435 found 5 days ago
*Available to Expedia members.