West Side Holidays

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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

Top hotels in West Side

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 Rp2.114.700 per night from 21 Dec to 22 Dec
Rp2.114.700
Rp2.482.445 total
21 Dec - 22 Dec
includes taxes & fees
8.8/10 Excellent! (1,728 reviews)
Friendly staff,clean and close to United Center

Reviewed on 30 Nov 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 Rp1.540.584 per night from 22 Dec to 23 Dec
Rp1.540.584
Rp1.808.492 total
22 Dec - 23 Dec
includes taxes & fees
9/10 Wonderful! (1,224 reviews)
The staff were awesome! This historic is great if you want a kitchen.

Reviewed on 4 Dec 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 Rp1.449.962 per night from 28 Dec to 29 Dec
Rp1.449.962
Rp1.702.042 total
28 Dec - 29 Dec
includes taxes & fees
9.6/10 Exceptional! (353 reviews)
Room was spacious with a great view. Staff was very friendly.

Reviewed on 3 Dec 2025

Hampton Inn & Suites Chicago Medical District UIC
See all 860 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.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park

Grant Park

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

What to do in West Side

Urbana–Champaign Scavenger Hunt: Hunting Illini

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

Rp205.922
per adult
Self-Guided Illinois Scavenger Hunt: The Great Quest in Illinois
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

Rp1.773.168
per adult
84% of travellers recommend
Chicago C3® by CityPASS®
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

Rp3.406.657
per adult
76% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
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 cancelling 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 travellers 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 travelling 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!
What months are the cheapest to book a flight to West Side?
An inexpensive month to land a fabulous deal to West Side is February, whereas prices are at their highest in December. Steer clear of this month if you're counting your pennies.
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.

How long is a flight to West Side?
It could take you an hour or more — it depends on which part of the States you're travelling from. The average flight times for these popular domestic routes to West Side will give you a better idea of what to expect:
  • Los Angeles, CA Airport (LAX-Los Angeles Intl.) to O'Hare Intl. Airport (ORD) - 3 hours and 58 minutes
  • Denver, CO Airport (DEN-Denver Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 36 minutes
  • Minneapolis, MN Airport (MSP-Minneapolis - St. Paul Intl.) to O'Hare Intl. Airport (ORD) - 1 hour and 44 minutes

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