Glenwood Vacation Packages
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Your Glenwood Vacation
Lock in a Glenwood vacation package and get ready to experience this amazing city the easy way. Think about staying in the neighborhood of South Deering, which is good for golfing and nature. Fill up your itinerary with tours of Coyote Run Golf Course, River Oaks Center and Ravisloe Country Club, some of the things you really should see during a trip to Glenwood. Stop daydreaming and start doing. Explore the multitude of options on Expedia today and finally put your Glenwood vacation plans into motion!
Top Glenwood vacation deals
- Swissotel - Chicago
Jan 7 - Jan 11Swissotel - Chicago + Flight
Downtown Chicago4 nights4.5 star property9.0/10 - Wonderful (3,566 reviews)"Breakfast was good"Reviewed November 4, 2026Roundtrip • Montreal (YUL) - Chicago (ORD)YUL - ORD • 1 stop ORD - YUL • 1 stopCA $1,051CA $758found 1 day agoper traveller - Sheraton Grand Chicago Riverwalk
Dec 19 - Dec 23Sheraton Grand Chicago Riverwalk + Flight
Downtown Chicago4 nights4.0 star property8.6/10 - Excellent (1,875 reviews)Roundtrip • Hamilton (YHM) - Chicago (ORD)YHM - ORD • 1 stop ORD - YHM • 1 stopCA $2,739CA $1,191found 18 hours agoper traveller - Park Hyatt Chicago
Dec 27 - Jan 2Park Hyatt Chicago + Flight
Downtown Chicago6 nights5.0 star property9.6/10 - Exceptional (1,001 reviews)"Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott. For example, there was a hair in the bed. When we reported it, the..."Reviewed November 4, 2026Roundtrip • Toronto (YTO) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YTZ • Nonstop - The Emily Hotel
Jan 7 - Jan 11The Emily Hotel + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (1,357 reviews)"Our stay at The Emily Hotel was outstanding! The entire property was well-maintained and the customer service provided by Leo and his team was excellent! We thoroughly enjoyed the offerings at Flora and were able to experience a Rooftop Cinema event! The hotel is conveniently located in walking distance to great restaurants and the L. I highly recommend The Emily Hotel and look forward to my stay during my next visit to Chicago!"Reviewed November 4, 2026Roundtrip • Montreal (YUL) - Chicago (ORD)YUL - ORD • 1 stop ORD - YUL • 1 stopCA $1,190CA $853found 1 day agoper traveller - Level Chicago Fulton Market
Jan 7 - Jan 11Level Chicago Fulton Market + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (602 reviews)"If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa. There was no housekeeping. Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before..."Reviewed November 4, 2026Roundtrip • Montreal (YUL) - Chicago (ORD)YUL - ORD • 1 stop ORD - YUL • 1 stopCA $1,044CA $760found 1 day agoper traveller
Glenwood Hotel Deals
Wind Creek Chicago Southland Casino and Hotel
Wind Creek Chicago Southland Casino and Hotel
Super 8 by Wyndham South Holland
Super 8 by Wyndham South Holland"Do not stay here."
Best Western Plus South Holland/Chicago Southland
Best Western Plus South Holland/Chicago Southland"Overall the place was clean, and breakfast was really good. However, the staff is rude and their attitudes are not friendly at all. The tone that is presented needs to be carefully assessed and carefully considered."
Quality Inn & Suites Harvey - Chicago Southland
Quality Inn & Suites Harvey - Chicago Southland
La Quinta Inn & Suites by Wyndham South Holland
La Quinta Inn & Suites by Wyndham South Holland
"Bad location I looked at the surroundings and left paid for the room and lost $100"
"It’s a clean place but a typical comfort in. Does not match the raving reviews. Should have gone with the Fairfield in for $20 more."
Econo Lodge South Holland - Chicago Southland
Econo Lodge South Holland - Chicago SouthlandFrequently Asked Questions
How much does a Glenwood vacation package cost?
Offering excellent value package deals from CA $758 on Expedia, you'll be pleasantly surprised at how much a vacation to Glenwood costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Glenwood?
January, February and November are the best times to search for cheap Glenwood vacation packages. Choosing to travel in quieter months means you'll typically find reduced prices on flights and hotels.
How many days is enough for Glenwood?
Dedicate at least 2 days for your Glenwood vacation in order to discover everything that makes this place unique. Wander around key areas, including East Hazel Crest and Ford Heights. Then tick off top attractions such as Midwest Carvers Museum and River Oaks Centre. With a clever itinerary, you'll be kept busy with room for some me-time too. Want to travel beyond Glenwood? Consider a day trip or two.
How to find the best Glenwood package deals?
Use Expedia's handy filters to find some great Glenwood package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Glenwood package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Glenwood vacation as a package?
You can enjoy significant savings on your Glenwood escape by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to view some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Glenwood?
Land incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Glenwood trip.
How to plan a trip to Glenwood?
- Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Glenwood.
- Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to experiences and flights. Your hotel will likely be the biggest expense during your trip to Glenwood.
- Decide how long to go for: Now that you know more about Glenwood, you can work out the perfect length of your vacation. Pull together a rough itinerary and give yourself enough time to cover everything you want to see.
- Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to choose a Glenwood vacation package that brings all your bookings together.