West Side Vacations from NT$29,422

Book a Hotel + Flight or Car together to unlock savings

Photo by throwingsofas

  • Plan, book, travel with confidence

  • Better together

    Save up to NT$5,067 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest West Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$43,745, price is now NT$29,422 per person
NT$29,422
per person
May 15 - May 19
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Big shoutout to Marina. Thank you for the hospitality and being so kind and helpful to me during my stay. Chicago is great!!

Reviewed on 2026/3/30

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$60,227, price is now NT$35,716 per person
NT$35,716
per person
May 15 - May 19
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Hotel was very clean, staff super friendly.

Reviewed on 2026/4/1

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$72,381, price is now NT$50,602 per person
NT$50,602
per person
May 15 - May 19
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
The staff were great. Amenities were also wonderful. Will come back.

Reviewed on 2026/3/31

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$60,844, price is now NT$43,198 per person
NT$43,198
per person
May 15 - May 19
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (2,019 reviews)
Wonderful location Nicely updated and appointed rooms. Quiet. Quick elevator. Excellent restaurant on site. Great value for money. Very helpful staff.

Reviewed on 2026/3/29

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was NT$49,006, price is now NT$34,831 per person
NT$34,831
per person
May 15 - May 19
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious

Reviewed on 2026/3/9

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
Blue Hour evening cityscape in West Loop neighborhood. Long exposure, nightscape architecture. Main street in Chicago, streets in Illinois.

West Loop

1 out of top 10 points of interest in this area

Consider a visit to Old St Patrick’s Church 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

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 NT$5,442 per night from Apr 5 to Apr 6
NT$5,442
NT$6,389 total
Apr 5 - Apr 6
includes taxes & fees
9.2/10 Wonderful! (1,328 reviews)
Place was very nice.

Reviewed on 2026/3/26

The Emily Hotel
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 NT$4,322 per night from Apr 12 to Apr 13
NT$4,322
NT$5,073 total
Apr 12 - Apr 13
includes taxes & fees
9/10 Wonderful! (2,047 reviews)
yes

Reviewed on 2026/3/31

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 NT$3,526 per night from Apr 5 to Apr 6
NT$3,526
NT$4,523 total
Apr 5 - Apr 6
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Staff was very friendly but the rooms weren’t that clean.

Reviewed on 2026/4/1

Holiday Inn & Suites Chicago - Downtown by IHG
See all 785 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

Tri Taylor

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 acclaimed theater scene in this vibrant area.

University of Illinois Chicago
Path with Yellow Flowers at the Humboldt Park Lagoon

Humboldt Park

Humboldt Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the acclaimed theater scene and entertainment choices in this vibrant area.

Humboldt Park
Garfield Park Conservatory

Garfield Park Conservatory

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

Garfield Park Conservatory

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.

Explore a world of travel with Expedia

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