Glenwood Vacations from ￥355,796

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The Latest Glenwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥467,374, price is now ￥355,796 per person
￥355,796
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (509 reviews)

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was ￥547,898, price is now ￥370,632 per person
￥370,632
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,041 reviews)

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Price was ￥675,684, price is now ￥495,208 per person
￥495,208
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,325 reviews)
The hotel is comfortable and well-maintained. It is located at the base of an L train. Stop that whisks passengers to Midway airport in 30 minutes. The location also gives access to Grant Park, State Street and the miracle mile. Rooms are large, comfortable and clean.

Reviewed on Aug 3, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ￥582,115, price is now ￥428,977 per person
￥428,977
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,606 reviews)
Overall I had a very good stay over there. My one complaint was there wasn't a microwave in the room.

Reviewed on Aug 3, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥591,690, price is now ￥440,253 per person
￥440,253
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,732 reviews)
There was no early check-in unfortunately. All staff were very friendly and helpful. Really grateful for the sturdy umbrellas in the room.

Reviewed on Aug 3, 2026

Find the Best Glenwood Vacation Packages

Glenwood Hotel Deals

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
Fully refundable
The price is ￥20,609 per night from Aug 13 to Aug 14
￥20,609
￥25,766 total
Aug 13 - Aug 14
includes taxes & fees
Holiday Inn Chicago – Midway Airport S by IHG
Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

3 out of 5
4900 S Lake Shore Dr Chicago IL
The price is ￥31,307 per night from Aug 9 to Aug 10
￥31,307
￥36,751 total
Aug 9 - Aug 10
includes taxes & fees
7/10 Good! (1,007 reviews)
"My room was clean, bed was clean. Very pleased with the room. Only down part was the drain was clogged in the shower. Staff was kind, the hallways were dirty and had a funky smell but didn’t smell it once I went into my room. Was visiting from out of state and was informed by more than one person ..."

Reviewed on Aug 3, 2026

Chicago Lake Shore Hotel
Sleep Inn Midway Airport Bedford Park

Sleep Inn Midway Airport Bedford Park

2.5 out of 5
6650 S Cicero Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥15,525 per night from Aug 25 to Aug 26
￥15,525
￥18,241 total
Aug 25 - Aug 26
includes taxes & fees
Sleep Inn Midway Airport Bedford Park
See all 910 properties in Glenwood
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Glenwood vacation package cost?
You can pick up a vacation package to this top destination from ￥355,796 on Expedia. But how much your vacation to Glenwood costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Glenwood?
January, February and November are great times to look for cheap Glenwood vacation packages. Choosing to travel in quieter months means you can typically find reduced prices on hotels and flights.
How many days is enough for Glenwood?
With a well-planned itinerary, you can easily visit the main Glenwood sights in a handful of days. But if you'd like to discover lesser-known spots or go on day trips, consider booking your Glenwood vacation for longer.
How to find the best Glenwood package deals?
Use Expedia's filters to help you find some of the best Glenwood package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Glenwood package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Glenwood vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still enjoy the flexibility to create a tailored Glenwood vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Glenwood?
If you've got your Glenwood vacation dates finalized, book early to snap up some awesome deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for quick escapes.
How to plan a trip to Glenwood?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Glenwood.
  2. Set a budget: Factor in costs such as flights, food and transportation when calculating how much to put aside for your trip to Glenwood. Then, choose a hotel that fits your budget, whether that's a low-cost option or a deluxe retreat.
  3. Decide how many days away: Start by compiling a list of the activities and attractions you'd like to experience in Glenwood. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick a Glenwood vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.