West Side Holidays

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Top Flight + Hotel Deals in West Side

Price found within the past 48 hours. Click for updated prices.
The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was €1,174, price is now €919 per person
€919
per person
7 Apr - 13 Apr
found 3 hours ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
8.4/10 Very Good! (1,444 reviews)
Room was very clean would return again

Reviewed on 23 Feb 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was €1,471, price is now €992 per person
€992
per person
7 Apr - 13 Apr
found 3 hours ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean rooms, excellent shower, but most importantly the best, friendly, helpful staff. Really enjoyed our stay.

Reviewed on 26 Feb 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €1,284, price is now €919 per person
€919
per person
7 Apr - 13 Apr
found 3 hours ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.

Reviewed on 16 Feb 2026

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was €1,264, price is now €960 per person
€960
per person
7 Apr - 13 Apr
found 3 hours ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Everything was great, I really enjoyed my stay!

Reviewed on 25 Feb 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was €1,250, price is now €962 per person
€962
per person
7 Apr - 13 Apr
found 3 hours ago
Return direct flight included
Porto (OPO) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
From beginning to the end my stay was a 10/10. I only stayed one night but that one night was worth it.

Reviewed on 24 Feb 2026

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

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 €110 per night from 2 Mar to 3 Mar
€110
2 Mar - 3 Mar
includes taxes & fees
9/10 Wonderful! (1,995 reviews)
Bathroom wasn’t clean and hair on towels

Reviewed on 25 Feb 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
9.2/10 Wonderful! (1,302 reviews)
Hotel is great. A lovely boutique venue. Friendly, professional and courteous staff made us feel very welcome.

Reviewed on 24 Feb 2026

Get rates
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 €134 per night from 8 Mar to 9 Mar
€134
8 Mar - 9 Mar
includes taxes & fees
9/10 Wonderful! (1,181 reviews)
Yes

Reviewed on 24 Feb 2026

Hyatt House Chicago West Loop
See all 836 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

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United Center

4.5/5(15 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

4.5/5(11 reviews)

Enjoy the student vibe at University of Illinois Chicago during your visit to Chicago. Stroll along the riverfront or experience the acclaimed art galleries 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 art galleries and fascinating museums in this vibrant area.

Humboldt Park

What to do in West Side

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

€37
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

€34
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

€32
per adult
98% of travellers recommend
Flyover in Chicago
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!
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.

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