
Glenwood Vacations from ¥257,628
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ¥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Glenwood Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Holiday Inn Express Chicago NW - Arlington Heights by IHG
Price was ¥271,323, price is now ¥257,628 per person
¥257,628
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,005 reviews)
Staff very nice and accommodating.
Hotel is in a decent area within 15 min from airport and most dining or shopping needs.
Reviewed on Jun 17, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was ¥371,260, price is now ¥328,276 per person
¥328,276
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
There charges are not clear, unnecessary security deposit, long hold period and I don't even know if they refunded my security deposit as haven't received any bill/receipt post checkout
Reviewed on Jun 18, 2026

Hilton Chicago O'Hare Airport
O'Hare
Price was ¥302,639, price is now ¥273,185 per person
¥273,185
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (2,329 reviews)
Always a great place to stay the night before an early international flight out of ORD. Staff at the front desk, restaurants, and cafe are all extremely friendly and helpful. At the Gaslight Club (old-style restaurant and piano bar), my friend said, "This is the best duck dish I have EVER had!"
Reviewed on Jun 19, 2026

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
Price was ¥281,780, price is now ¥265,432 per person
¥265,432
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,894 reviews)
This property is right by the airport making it very convenient. It is clean with spacious rooms and very comfortable bedding . We missed the free breakfast time but they were so nice and turned the pancake machine back on and made sure we got everything that we asked for😊Also practically in the same parking lot is a McDonald’s a Popeyes and another Italian fast food. This hotel is in an ideal location. I would recommend it …and the price is very reasonable.
Reviewed on Jun 17, 2026

Hyatt Regency O'Hare Chicago
Price was ¥274,172, price is now ¥259,876 per person
¥259,876
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,637 reviews)
It’s our go-to place near the O’Hare Airport. Clean, safe, great amenities and friendly staff. I like the newly renovated rooms, too.
No complaints!
Reviewed on Jun 19, 2026
Find the Best Glenwood Vacation Packages
Glenwood Hotel Deals

Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥19,593 per night from Jul 5 to Jul 6
¥19,593
¥24,615 total
Jul 5 - Jul 6
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"Really enjoyed the hotel very comfortable"
Reviewed on Jun 19, 2026

Sleep Inn Midway Airport Bedford Park
6650 S Cicero Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥19,762 per night from Jul 1 to Jul 2
¥19,762
¥23,216 total
Jul 1 - Jul 2
includes taxes & fees
8/10 Very Good! (1,920 reviews)
"Love the free shuttle They have the best coffee in town"
Reviewed on Jun 19, 2026

Wind Creek Southland Casino and Hotel
17300 S Halsted St Hazel Crest IL
Fully refundableReserve now, pay when you stay
The price is ¥23,536 per night from Jun 22 to Jun 23
¥23,536
¥26,355 total
Jun 22 - Jun 23
includes taxes & fees
9.2/10 Wonderful! (445 reviews)
"Great location off the highway. Short travel distance into downtown Chicago. Great stay!"
Reviewed on Jun 19, 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
