Montclare Holidays

Book a Hotel + Flight or Car together to unlock savings

Where to stay in Montclare

Find the best Montclare areas and neighborhoods for the activities you enjoy most. Learn more about Montclare

A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Lake Michigan are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Lake Michigan and Michigan Avenue are a few top attractions in The Loop. Hop around the city on the metro at Washington Station or Lake Station and check out the area's fascinating museums, popular shops and acclaimed art galleries.

A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Are you interested in fascinating museums, panoramic lake views and popular shops? A visit to Magnificent Mile might be the perfect thing. You can also explore top sights like Michigan Avenue and Chicago Water Tower.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

Top hotels in Montclare

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

3.001.975 ₫

3.569.047 ₫ total

8 Sept - 9 Sept

includes taxes & fees

8/10 Very good! (10,288 reviews)

"Lower price$"

Reviewed on 11 Aug 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

3.740.238 ₫

4.446.770 ₫ total

30 Aug - 31 Aug

includes taxes & fees

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Fully refundableReserve now, pay when you stay

6.111.642 ₫

7.174.458 ₫ total

12 Sept - 13 Sept

includes taxes & fees

See all 4,818 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 holiday package cost?

Live it up in Montclare from as low as . 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 holiday packages mean plenty of savings for the savvy traveller. 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 1null000null000 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 Centre is another sight in Montclare that people flock to.

How far in advance should I book my Montclare holiday?

It can be difficult to know when is the ideal time to book your Montclare holiday. 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 travelling 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 holiday package is the most convenient way to organise 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 holiday 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 holiday 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.