West Side Vacations from ￥141,726

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The Latest West Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was ￥190,052, price is now ￥141,726 per person
￥141,726
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city

Reviewed on Nov 26, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥347,468, price is now ￥231,547 per person
￥231,547
per person
Feb 19 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Everything perfect , comfortable room , nice staff make out stay unforgettable.

Reviewed on Nov 27, 2025

Chicago luxury home suites

Chicago luxury home suites

2 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥476,096, price is now ￥338,364 per person
￥338,364
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
10/10 Exceptional! (1 review)
Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.

Reviewed on Nov 26, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥315,344, price is now ￥232,656 per person
￥232,656
per person
Jan 1 - Jan 6
found 18 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.

Reviewed on Nov 26, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥196,586, price is now ￥148,130 per person
￥148,130
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
My husband and I were on our Honeymoon & we missed our flight. Meaning our third party reservation through Expedia was going to charge us for the day we missed. But when we arrived to Hotel Riu, Anderson helped us promptly. He didn’t charge us fees for the day we missed. He checked us in right away with no problems or delays. This hotel is absolutely beautiful, clean, and comfortable. The bar drinks are so delicious and they do not skimp out on the alcohol. The rooftop is beautiful, with good food, and a fun glass ledge. Also, their breakfast is included and it was delicious. It’s a perfect selection of baked goods & breakfast food. The location is also top tier. It’s close to all the shops and Starbucks Reserve Roastery. It wasn’t far from the Riverwalk, LondonHouse, and other attractions. I will be bringing my family back here. I had the best time!

Reviewed on Nov 27, 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
Fully refundable
The price is ￥19,872 per night from Dec 22 to Dec 23
￥19,872
￥23,327 total
Dec 22 - Dec 23
includes taxes & fees
8.8/10 Excellent! (1,707 reviews)
The location was good. Close to the train station. Staff was very nice and we were able to check in early. Yay!

Reviewed on Nov 26, 2025

Crowne Plaza Chicago West Loop by IHG
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 ￥17,137 per night from Dec 7 to Dec 8
￥17,137
￥20,117 total
Dec 7 - Dec 8
includes taxes & fees
9/10 Wonderful! (1,220 reviews)
Everything

Reviewed on Nov 27, 2025

Hyatt House Chicago Medical/University District
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
710 S Seeley Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥13,623 per night from Dec 7 to Dec 8
￥13,623
￥15,991 total
Dec 7 - Dec 8
includes taxes & fees
9.6/10 Exceptional! (348 reviews)
Room was very clean and comfortable. Would have appreciated a disposable bathroom glass for use when brushing teeth or taking a pill. Had to take a cup from the coffee station.

Reviewed on Nov 26, 2025

Hampton Inn & Suites Chicago Medical District UIC
See all 855 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

4.5/5(701 reviews)

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

4/5(832 reviews)

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

University of Illinois Chicago
Garfield Park Conservatory showing a park

Garfield Park Conservatory

4/5(3 reviews)

While away the afternoon in this huge conservatory housing tropical and rare plants, waterfalls and art.

Garfield Park Conservatory

What to do in West Side

Urbana–Champaign Scavenger Hunt: Hunting Illini

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

￥1,879
per adult
Self-Guided Illinois Scavenger Hunt: The Great Quest in Illinois
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,926
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,866
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.