West Side Vacations from ￥213,600

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The Latest West Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥250,738, price is now ￥213,600 per person
￥213,600
per person
Dec 27 - Dec 30
found 10 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Healthy breakfast and very clean hotel with friendly staff.

Reviewed on Oct 10, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥325,108, price is now ￥259,054 per person
￥259,054
per person
Dec 27 - Dec 30
found 10 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Very clean very nice hotel. Easy accesss to restaurants and shopping.

Reviewed on Oct 11, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was ￥309,135, price is now ￥258,976 per person
￥258,976
per person
Dec 27 - Dec 30
found 11 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
We have stayed at every luxury property in Chicago and when coming to visit we always stay at the Park Hyatt. The rooms are spectacular!

Reviewed on Oct 10, 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥404,586, price is now ￥344,647 per person
￥344,647
per person
Dec 26 - Jan 2
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (294 reviews)
Great place to stay.

Reviewed on Oct 10, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was ￥279,562, price is now ￥241,498 per person
￥241,498
per person
Dec 27 - Dec 31
found 11 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.2/10 Very Good! (2,123 reviews)
No water pressure -- but high pressure sales for basic internet. Rooms were last updated about 15 years ago. All in all, a 3.5 star experience at a 5 star price. They've got the location, but you should only be staying here as a last resort.

Reviewed on Oct 11, 2025

Where to stay in West Side

Find the best West Side areas and neighborhoods for the activities you enjoy most. Learn more about West Side
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West Loop

1 out of top 10 points of interest in this area

Consider a visit to Milwaukee Avenue and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.

Find hotels in West Loop

Find the Best West Side Vacation Packages

West Side Hotel Deals

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
The price is ￥19,655 per night from Nov 9 to Nov 10
￥19,655
￥23,074 total
Nov 9 - Nov 10
includes taxes & fees
8.8/10 Excellent! (1,576 reviews)
"I was glad but surprised that my package included parking. We never left, but upon check out, the gate wouldn’t go up, and the machine told us to pay. I went to tell the front desk, and the worker came out and made the gate go up for us!"

Reviewed on Oct 6, 2025

Crowne Plaza Chicago West Loop by IHG
The Emily Hotel

The Emily Hotel

4 out of 5
311 North Morgan Street, Chicago, IL
The price is ￥83,664 per night from Oct 21 to Oct 22
￥83,664
￥98,214 total
Oct 21 - Oct 22
includes taxes & fees
9/10 Wonderful! (1,240 reviews)
"Perfect location and atmosphere"

Reviewed on Oct 7, 2025

The Emily Hotel
Hyatt House Chicago Medical/University District

Hyatt House Chicago Medical/University District

3.5 out of 5
1835 West Harrison Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥22,981 per night from Nov 2 to Nov 3
￥22,981
￥26,976 total
Nov 2 - Nov 3
includes taxes & fees
8.8/10 Excellent! (1,145 reviews)
"Perfect as always we love coming into the city and staying here. You're close to everything. Rooms provide everything you could need and decently priced"

Reviewed on Oct 6, 2025

Hyatt House Chicago Medical/University District
See all 798 properties in West Side
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.

Discover the most popular places to visit in West Side

Blackhawks 5x4 Leafs

United Center

Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

United Center
University of Illinois Chicago

University of Illinois Chicago

Enjoy the collegiate vibe at University of Illinois Chicago during your stay in Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

University of Illinois Chicago
Garfield Park Conservatory showing a park

Garfield Park

After visiting Garfield Park, make a plan to see the other sights and activities in Chicago. Discover the top-notch restaurants and acclaimed theater scene in this vibrant area.

Garfield Park

What to do in West Side

Urbana–Champaign Scavenger Hunt: Hunting Illini

Self-Guided Illinois Scavenger Hunt: The Great Quest in Illinois

￥1,803
per adult
Self-Guided Illinois Scavenger Hunt: The Great Quest in Illinois
River tour boat in Chicago

Architecture River Tour

￥7,144
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

￥6,486
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
See all activities in West Side

Frequently asked questions

Can I cancel my flight booking to West Side due to COVID-19?
Our Customer Service Portal has useful information about changing or canceling your flight due to COVID-19. Before booking your tickets, it's wise to check the terms and conditions of your chosen airline too.
What's the best way to find cheap flights to West Side that have flexible change policies?
At Expedia, we've been channeling our inner yoga master to get you the most flexible airfares around town. Simply check the "No change fee" box directly beneath the filter subheading "Flexible change policies" to find your dream flight to West Side.
What are some of the general tips for travelers to West Side during the COVID-19 outbreak?
COVID-19 has led to substantial changes to how we travel. If you're planning a trip to West Side, the following tips will help you navigate this new traveling reality:
  • Before booking anything, check if any travel bans or restrictions apply — in both your destination and origin. Get the latest updates by reviewing government travel advisories.
  • Requirements state you must wear a face mask at the airport, including at screening checkpoints. Be ready to lower your mask for ID purposes when asked by a TSA employee.
  • Rather than handing a TSA agent your boarding pass, place it directly on the reader yourself. When that's done, hold it up for inspection.
  • TSA is now allowing passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on baggage. This will need to be removed from your bag for screening.
  • Place any personal items (like your phone, wallet and keys) in your carry-on rather than a bin to minimize handling during the screening process.
  • Separate any food you have for X-ray scanning. Food items often trigger the alarm. Putting them in a clear plastic bag and into a bin reduces the need for a TSA agent to touch and inspect your belongings.

Which airlines fly to West Side?
Let American Airlines take you there. This leading carrier schedules 13307 flights each month to O'Hare Intl. Airport (ORD), a West Side gateway.
How can I find cheap tickets to West Side?
A useful strategy for nabbing cheap fares is to be flexible with your travel dates. Start by searching for your flight to West Side, then click on the "flexible dates" box for a list of prices for nearby days. Another handy tip? Book well ahead of time. To give you an idea of fares, was the lowest price for a flight to West Side in the last seven days.
How much is a flight to West Side?
If you were flying one way from (), you could've snapped up an affordable ticket for in the last seven days. Round-trip flights to West Side ranged from only to over the same period.
What are the most popular airports to fly into in West Side?
West Side's main entry point is O'Hare Intl. Airport (ORD). Get your next big journey underway by securing an airfare on one of the 33491 flights a month to this destination.
When is the cheapest time to fly to West Side?
Flying on a Tuesday, followed by a Monday, is generally the best way to get the cheapest deal. Stay away from the weekends if you can, because Saturday is typically the most expensive day. Spend the money you saved enjoying yourself in West Side instead!
How much is a plane ticket to West Side?
In the last seven days, fares cost between and . Scroll through our amazing deals to West Side, make a booking and then get ready for your getaway!
Which airlines with flights to West Side employ COVID-19 cleanliness policies?
To reduce contact between passengers and flight attendants during the global COVID-19 pandemic, most reputable airlines have taken social distancing and other strategies to the skies. Just a few of these are:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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