West Chicago Holidays

Photo by Khryz Garcia

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Top Flight + Hotel Deals in West Chicago

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was €1,182, price is now €723 per person
€723
per person
13 Nov - 19 Nov
found 12 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on 25 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €2,320, price is now €1,397 per person
€1,397
per person
13 Nov - 19 Nov
found 12 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on 25 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,734, price is now €1,057 per person
€1,057
per person
13 Nov - 19 Nov
found 12 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,489, price is now €975 per person
€975
per person
13 Nov - 19 Nov
found 12 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on 26 Aug 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €1,287, price is now €852 per person
€852
per person
13 Nov - 19 Nov
found 12 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on 27 Aug 2025

Top hotels in West Chicago

Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €153 per night from 19 Sept to 20 Sept
€153
19 Sept - 20 Sept
includes taxes & fees
Marriott Chicago O'Hare
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €180 per night from 19 Sept to 20 Sept
€180
19 Sept - 20 Sept
includes taxes & fees
8.2/10 Very Good! (2,101 reviews)
Passing Thru
"Nice quiet and convenient hotel and room. Excellent staff."

Reviewed on 24 Aug 2025

Hilton Chicago O'Hare Airport
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 €140 per night from 13 Sept to 14 Sept
€140
13 Sept - 14 Sept
includes taxes & fees
Hyatt Regency O'Hare Chicago
See all 1,251 properties in West Chicago
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.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

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
Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home 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

Navy Pier

4/5(125 reviews)

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

Navy Pier

What to do in West Chicago

River tour boat in Chicago

Architecture River Tour

€36
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

€35
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

€39
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in West Chicago

Frequently asked questions

How much does a West Chicago holiday package cost?
You can snap up a holiday package to this destination from €723 on Expedia. However, how much your holiday to West Chicago costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to West Chicago?
You can usually find reduced prices and better availability in January, September and December. Browse our cheap West Chicago holiday packages and you could land some excellent off-season deals.
How many days is enough for West Chicago?
With a well-organised schedule, you can easily hit the top West Chicago sights in a few days. But if you'd like to discover hidden gems or take day trips, think about booking your West Chicago holiday for longer.
Is it worth booking a holiday package to West Chicago?
Known for its nature, golfing and a host of other highlights, you can be certain West Chicago is a good holiday destination. Some of the most popular attractions to put on your itinerary? Visit St Andrews Golf and Country Club and Prairie Landing during your West Chicago holiday.
How to find the best West Chicago package deals?
Landing a cheap West Chicago package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget range, add some filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most pocket-friendly West Chicago package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a West Chicago holiday as a package?
You can enjoy significant savings on your West Chicago escape by booking a tailored holiday package. Check the "Package" heading, then select your travel dates and destination to browse some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to West Chicago?
If you're considering a spontaneous West Chicago getaway, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your flights and hotels by booking ahead.
How to plan a trip to West Chicago?

  1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to visit West Chicago.
  2. Budget wisely: Besides the price of your accommodation, you'll need to consider other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected costs that could crop up during your trip to West Chicago.
  3. Decide how long to go for: Now that you're up to speed on West Chicago, you can work out the perfect length of your holiday. Put together a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a personalised West Chicago holiday package.

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