Montclare Holidays

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Price found within the past 48 hours. Click for updated prices.
  • 2 restaurants; breakfast, lunch and dinner served
    Jul 30 - Aug 3

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (3,730 reviews)
    "We stayed in this hotel in our daughter's wedding weekend. It was wonderful, the river and city view from our 18th story room was spectacular. I recommend it to.all ages."
    Reviewed June 7, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,713
    £1,296
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Terrace/patio
    Jul 30 - Aug 3

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,534 reviews)
    "This is an amazing place. Everything you can think of all under 1 roof. My hotel view was amazing. I am looking forward to coming annually."
    Reviewed June 8, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,877
    £1,398
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Full-sized fridge, microwave, oven, stovetop
    Aug 20 - Aug 25

    Level Chicago – Old Town + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.0/10 - Wonderful (489 reviews)
    "Very clean and loved the location and amenities with the store on the first floor was fantastic"
    Reviewed June 3, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £1,964
    £1,495
    per traveller
    found 8 hours ago
    Level Chicago – Old Town
  • Dinner served
    Jul 30 - Aug 4

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,000 reviews)
    "Nice staff clean room would stay again."
    Reviewed June 6, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £2,062
    £1,606
    per traveller
    found 1 day ago
    Kimpton Gray Hotel by IHG
  • Breakfast and dinner served
    Jul 30 - Aug 3

    Omni Chicago Hotel + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,798 reviews)
    "All around great property and a wonderful location"
    Reviewed June 9, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,701
    £1,330
    per traveller
    found 1 day ago
    Omni Chicago Hotel

Where to stay in Montclare

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

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

Top hotels in Montclare

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 £121 per night from 29 Jun to 30 Jun
£121
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,228 reviews)
"Housekeeping did not come a single time in the four days and four nights I stayed there. The beds were not made nor was the trash taken out a single time . I had to phone them twice to receive bath towels. I was using Uber eats take out bags as trash bags due to the lack of housekeeping not ..."

Reviewed on 9 Jun 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is £142 per night from 1 Jul to 2 Jul
£142
1 Jul - 2 Jul
includes taxes & fees
7.8/10 Good! (1,547 reviews)
"Everything perfect"

Reviewed on 9 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is £136 per night from 28 Jun to 29 Jun
£136
28 Jun - 29 Jun
includes taxes & fees
8.8/10 Excellent! (2,638 reviews)
"Upsetting that I was given a room that I had to haul all of my luggage up 16 steep stairs. No other room options. I had reserved a room months in advance. The front desk lady said a few stairs, which I found odd being that there is an elevator. Beware…the top floor is by stairs only! Front desk lady ..."

Reviewed on 9 Jun 2026

Hyatt Regency O'Hare Chicago
See all 4,909 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Montclare travel package cost?
Our Montclare travel packages, which begin at just , are an easy way to save big bucks. Select your favourite hotels, flights and rental car to create a custom-built escape.
If I'm not able to travel, can I cancel my Montclare travel package?
Yes, it's possible to cancel your Montclare booking if your plans have changed. Whether you'll incur a fee or not depends on your hotel, airline or car rental company. It may be possible to change or cancel your booking for free if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.
How do I get a cheap travel package to Montclare?
Bundle, bundle, bundle. Flights, rental cars and hotels — combine whatever you need into a Montclare travel package to save a ton of cash. Score even more deals when you include extras such as sightseeing tours to your booking. But that's not the only good part. You have the flexibility to tailor your holiday your own way. We offer over 550 airlines and 1,000,000 hotels globally, so that everyone has an opportunity to travel and live out those holiday dreams.
Does Expedia offer Book Now, Pay Later Montclare holidays?
We sure do. Expedia has partnered with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply choose the payment plan that suits you best during the checkout process and take away the stress of budgeting for your next trip. Be sure to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that work for all budgets, so you can have that well-deserved holiday sooner.
  • Pay in instalments holidays: If you want to pay for your escape in multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Clicking the "book now" button is easier with this payment option. Just put down a small deposit on your booking and then start packing your suitcase.

What are the top hotels in Montclare?
Whether you'll be staying for one or several nights in Montclare, you'll get a solid night's sleep at Lovely One Bedroom Modern Condo. This option is the first choice for many travellers.
How far in advance should I book my Montclare holiday?
Travellers are usually able to look up international airfares on Expedia up to a year in advance of departure. Booking last minute? With a little bit of luck, it's still possible to purchase a cheap ticket just weeks before your flight.
What does an Expedia Montclare travel package include?
Rental cars, flights and hotels, or any combination of the three — it's totally up to you. Whether you're venturing to Montclare with the whole family or enjoying a solo break, there's a package to suit every budget and style. Once you've made your booking, why not add on some activities?
What should I know before booking a Montclare travel package?
You'll save plenty with an Expedia travel package. Combine your airfares, rental cars and hotels and unlock fabulous discounts. You're not limited to hotels, though. Book with us and take your pick of beachfront villas, creek-side mountain cabins and even treehouses and ranches!
Can I choose my airline with a Montclare Expedia travel package?
Expedia offers access to more than 550 airline partners worldwide, so you definitely can. Simply choose your favourite carrier and craft your ideal Montclare holiday.

Popular places to visit

Wrigley Field

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
Navy Pier

Navy Pier

4/5(127 reviews)

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

Navy Pier
Millennium Park

Millennium Park

4.5/5(147 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£81
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
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. Flight-inclusive packages are ATOL protected.