Montclare Vacations from ￥242,386

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The Latest Montclare Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
Downtown Chicago
Price was ￥272,044, price is now ￥242,386 per person
￥242,386
per person
Oct 5 - Oct 10
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,825 reviews)
Excellent location and accommodations. The only disappointment was the indoor pool, as it was not heated, although hotel website states it is.

Reviewed on Sep 3, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was ￥481,088, price is now ￥378,840 per person
￥378,840
per person
Oct 5 - Oct 10
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!

Reviewed on Aug 31, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was ￥328,690, price is now ￥269,942 per person
￥269,942
per person
Oct 5 - Oct 10
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (286 reviews)
The staff were excellent

Reviewed on Aug 21, 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was ￥542,698, price is now ￥463,804 per person
￥463,804
per person
Oct 5 - Oct 10
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on Aug 12, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was ￥519,605, price is now ￥452,942 per person
￥452,942
per person
Oct 5 - Oct 10
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Truly enjoyed our experience at this hotel. Staff very kind and helpful. Location was perfect because of its location on the Magnificent Mile and getting to other areas of interest in Chicago. The room was very comfortable and clean. Definitely recommend this hotel!

Reviewed on Sep 4, 2025

Where to stay in Montclare

Find the best Montclare areas and neighborhoods for the activities you enjoy most. Learn more about Montclare
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Montclare Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥29,337 per night from Oct 4 to Oct 5
￥29,337
￥34,440 total
Oct 4 - Oct 5
includes taxes & fees
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥26,376 per night from Sep 14 to Sep 15
￥26,376
￥30,962 total
Sep 14 - Sep 15
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥24,794 per night from Sep 22 to Sep 23
￥24,794
￥29,106 total
Sep 22 - Sep 23
includes taxes & fees
The Wade
See all 4,877 properties in Montclare
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 Montclare vacation package cost?
Live it up in Montclare from as low as ￥242,386. Choose from a great selection of flights, hotels and rental cars to suit your budget. Pick up even more discounts when you add some tours or activities to your package.
How do I get a cheap travel package to Montclare?
Our Montclare vacation packages mean plenty of savings for the savvy traveler. For the best deal, simply combine your flights, hotels and tours into a budget-friendly package. But impressive bargains are just the beginning of your next unforgettable adventure. When you book with Expedia, you'll have more than 550 air carriers and 1,000,000 properties throughout the world to choose from. No matter your budget or style, there's a package that's perfect for you.
Where should I stay in Montclare?
With fascinating attractions like Portage Park and Six Corners in this area, look for a hotel located near either one. Community First Medical Center is another sight in Montclare that people flock to.
How far in advance should I book my Montclare vacation?
It can be difficult to know when is the ideal time to book your Montclare vacation. But generally the earlier you book, the more affordable the prices. Sometimes, you can book your flights and hotels nearly a year before departure. If you're considering a last-minute getaway, no need to worry! There are incredible bargains posted on Expedia every day.
What does an Expedia Montclare travel package include?
It comes down to what you're after. If you're traveling solo, you might decide to combine hotels and flights. Bringing the whole family to Montclare? A travel package that includes rental cars, flights and hotels might suit you better. Expedia gives you the flexibility to tailor your travel package.
What should I know before booking a Montclare travel package?
Bundling your bookings into a Montclare vacation package is the most convenient way to organize your trip. Not only that, you'll save big when you combine your flights, hotels and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with a Montclare Expedia vacation package?
Expedia has access to more than 550 airline partners worldwide, so you sure can! Simply choose your preferred air carrier and put together the perfect Montclare trip.
If I'm not able to travel, can I cancel my Montclare vacation package?
If your travel plans in Montclare have changed, it's comforting to know that it's possible to cancel your booking. If you made your booking in the last 24 hours, you may be able to receive a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose fees. For more information, visit our Customer Service Portal.

Discover the most popular places to visit in Montclare

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

￥6,127
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥5,986
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

￥6,651
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.