West Side Holidays from £730

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Top West Side Flight + Hotel Deals

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 £1,134, price is now £730 per person
£730
per person
10 May - 14 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
This was a great stay! Really enjoyed the breakfast! Only down side was the shower. Water did not get hot and water pressure was horrible. Otherwise would have been 5 stars!

Reviewed on 21 Feb 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,959, price is now £1,336 per person
£1,336
per person
7 May - 14 May
found 24 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
First off I want to give a special shout out to Eric! He assisted us so well in every way possible. I also didn’t expect it to be such a nice condo complex but I was so impressed by the rooms, amenities and the workers. Will definitely be coming back very soon!

Reviewed on 19 Feb 2026

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was £1,409, price is now £985 per person
£985
per person
7 May - 14 May
found 24 hours ago
Return flight included
London (LON) to Chicago (ORD)
8.4/10 Very Good! (1,444 reviews)
The lakeside view. Also the room was clean and spacious.

Reviewed on 19 Feb 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,393, price is now £1,681 per person
£1,681
per person
27 Apr - 4 May
found 14 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Great hotel, plus excellent service me and my wife like it we definitely coming back thanks

Reviewed on 17 Feb 2026

Graduate by Hilton Evanston

Graduate by Hilton Evanston

4 out of 5
Downtown Evanston
Price was £1,662, price is now £1,171 per person
£1,171
per person
27 Apr - 4 May
found 14 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.8/10 Excellent! (1,001 reviews)
Best location if you are visiting Northwestern. Close to everything. Nicely decorated and very clean.

Reviewed on 19 Feb 2026

The Annual Holiday Sale

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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
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 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

West Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

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 £109 per night from 22 Feb to 23 Feb
£109
22 Feb - 23 Feb
includes taxes & fees
8.8/10 Excellent! (1,981 reviews)
😊

Reviewed on 17 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
The price is £110 per night from 1 Mar to 2 Mar
£110
1 Mar - 2 Mar
includes taxes & fees
9/10 Wonderful! (1,301 reviews)
Staff very cordial and competent at all phases from valet to check in to the restaurant bar.

Reviewed on 16 Feb 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
The price is £118 per night from 1 Mar to 2 Mar
£118
1 Mar - 2 Mar
includes taxes & fees
8.8/10 Excellent! (1,191 reviews)
staff very accommodating and room, super comfortable and quiet!

Reviewed on 15 Feb 2026

Hyatt House Chicago West Loop
See all 845 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Chicago_UnitedCenter_6064077_01

United Center

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
Garfield Park Conservatory which includes a park

Garfield Park Conservatory

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

Garfield Park Conservatory

What to do in West Side

Flyover in Chicago

Flyover in Chicago

£28
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
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

£18
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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. Flight-inclusive packages are ATOL protected.