Near West Side Vacations from ￥207,270

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  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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The Latest Near 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 ￥250,590, price is now ￥207,270 per person
￥207,270
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Friendly staff, tasteful room

Reviewed on Feb 11, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was ￥348,173, price is now ￥270,984 per person
￥270,984
per person
May 1 - May 5
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Hot tub wasn’t working(freezing cold) and no robes in my room. Need bigger roller carts and cheaper or free parking. Other than that the room, view, amenities were excellent.

Reviewed on Feb 9, 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was ￥308,092, price is now ￥255,944 per person
￥255,944
per person
May 1 - May 6
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Food at sports bar was great along with the service. Bedding was top notch, room clean& nice TV

Reviewed on Feb 9, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥310,404, price is now ￥260,047 per person
￥260,047
per person
Apr 15 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.

Reviewed on Feb 3, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was ￥296,446, price is now ￥249,950 per person
￥249,950
per person
Apr 7 - Apr 11
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9/10 Wonderful! (2,947 reviews)
Great room. Beautiful view. Wonderful service from the staff.

Reviewed on Feb 11, 2026

Where to stay in Near West Side

Find the best Near West Side areas and neighborhoods for the activities you enjoy most. Learn more about Near West Side
Downtown Chicago showing a city

Downtown Chicago

4 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

Near 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 refundableReserve now, pay when you stay
The price is ￥15,853 per night from Feb 16 to Feb 17
￥15,853
￥18,611 total
Feb 16 - Feb 17
includes taxes & fees
8.8/10 Excellent! (1,962 reviews)
Clean room, comfortable bed, friendly staff, good location

Reviewed on Feb 10, 2026

Crowne Plaza Chicago West Loop by IHG
The Emily Hotel

The Emily Hotel

4 out of 5
311 North Morgan Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥39,012 per night from Feb 21 to Feb 22
￥39,012
￥45,796 total
Feb 21 - Feb 22
includes taxes & fees
9/10 Wonderful! (1,304 reviews)
Room size was great. Very comfortable. Clean. Nice view

Reviewed on Feb 8, 2026

The Emily Hotel
Hyatt House Chicago West Loop

Hyatt House Chicago West Loop

3.5 out of 5
105 N MAY STREET Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥22,249 per night from Feb 20 to Feb 21
￥22,249
￥26,119 total
Feb 20 - Feb 21
includes taxes & fees
8.8/10 Excellent! (1,186 reviews)
-

Reviewed on Feb 10, 2026

Hyatt House Chicago West Loop
See all 4,956 properties in Near 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.

Frequently asked questions

How much does a Near West Side vacation package cost?
Custom build your Near West Side package from a low ￥207,270. Choose from any combination of rental cars, flights and hotels to craft the trip you've been dreaming about for ages. Don't forget to add on a few activities!
How do I get a cheap travel package to Near West Side?
Our Near West Side vacation packages mean plenty of savings for the savvy traveler. For the best deals, simply combine your hotel, flights and extras (including tours) into a convenient package. But great bargains are just the beginning of your next big adventure. Book with Expedia and you'll have more than 550 air carriers and 1,000,000 properties around the world to select from. Whatever your budget, there's a package with your name on it.
Where should I stay in Near West Side?
Make sightseeing a breeze by staying just around the corner from Near West Side's big attractions. University of Illinois Chicago and United Center are two of the most popular.
What are the top hotels in Near West Side?
If it's your first time in Near West Side, lock in a room at Hyatt House Chicago Medical/University District or Hyatt Place Chicago Medical/University District. Both hotels offer comfortable beds and are favorites among lots of travelers.
How far in advance should I book my Near West Side vacation?
It's difficult to pick the best time for airfares, but we usually say the earlier, the better. Plenty of international journeys on Expedia become available to compare up to 12 months in advance. If you're booking late, don't despair. Low prices appear from time to time within a few weeks of departure dates.
What does an Expedia Near West Side travel package include?
Hotels, flights and a cool set of wheels for your road trip adventures. Simply pick and choose your preferred bundle and get access to great discounts. Once you've made your booking, add on a couple of activities and tours and watch your savings pile up. When it comes to creating your Near West Side escape, you're the boss!
What should I know before booking a Near West Side travel package?
A travel package can be easier on the wallet than individually booking all you need for your adventure. For example, bundle your hotels, flights and rental cars and save a tidy sum. Whatever kind of vacation you're planning, you're bound to find a package that's perfect for you.
Can I choose my airline with a Near West Side Expedia vacation package?
Yes, you're in control. Expedia has access to more than 550 partner airlines around the world, so you can design your Near West Side vacation according to your travel needs.
If I'm not able to travel, can I cancel my Near West Side vacation package?
Because we know life can be unpredictable, the answer is yes. For further details, check out our Customer Service Portal. But generally speaking, if you've booked your Near West Side vacation package in the last 24 hours, you may be able to cancel or change it for no charge. Your airline, hotel or car rental company may charge a fee if you made your booking a while ago.

Discover the most popular places to visit in Near West Side

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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 entertainment choices.

United Center
Tri Taylor

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

Rush University Medical Center

4.5/5(14 reviews)

Though Rush University Medical Center might be what brings you to town, perhaps you'll have a chance to explore more of Chicago while you are here.

Rush University Medical Center

Things to do

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,883
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,341
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Art Institute of Chicago

Art Institute of Chicago

￥6,325
per adult
92% of travellers recommend
Art Institute of Chicago
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.