Near West Side Vacations from ￥200,594

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    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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was ￥256,630, price is now ￥200,594 per person
￥200,594
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Amazing room view great service just no microwave that’s all they need

Reviewed on Dec 27, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥385,898, price is now ￥274,520 per person
￥274,520
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Absolutely loved the hotel.Grand Dulxe Suite was huge with amazing views.All staff top notch.

Reviewed on Dec 27, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was ￥399,685, price is now ￥297,235 per person
￥297,235
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Beautifully decorated for Christmas. Spotless as always.

Reviewed on Dec 27, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was ￥271,780, price is now ￥207,398 per person
￥207,398
per person
Feb 11 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Early check in available for $25, worth it for getting rest between flights. Very friendly staff

Reviewed on Dec 27, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was ￥285,935, price is now ￥221,613 per person
￥221,613
per person
Mar 15 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.

Reviewed on Dec 18, 2025

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

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

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 ￥14,232 per night from Jan 8 to Jan 9
￥14,232
￥16,707 total
Jan 8 - Jan 9, 2026
includes taxes & fees
8.8/10 Excellent! (1,800 reviews)
Price was great for the quality.

Reviewed on Dec 26, 2025

Crowne Plaza Chicago West Loop by IHG
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
Fully refundable
The price is ￥16,440 per night from Dec 30 to Dec 31
￥16,440
￥21,179 total
Dec 30 - Dec 31
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
Excellent

Reviewed on Dec 21, 2025

Holiday Inn & Suites Chicago - Downtown by IHG
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 ￥14,279 per night from Jan 4 to Jan 5
￥14,279
￥16,761 total
Jan 4 - Jan 5, 2026
includes taxes & fees
9.6/10 Exceptional! (388 reviews)
Enjoyed our stay! The room was great and the staff were so friendly and helpful especially Elena! Thank you Elena for all your help.

Reviewed on Dec 27, 2025

Hampton Inn & Suites Chicago Medical District UIC
See all 4,840 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 ￥200,594. 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

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 art 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 entertainment choices 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

River tour boat in Chicago

Architecture River Tour

￥6,839
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

￥6,310
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,827
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.