West Side Holidays from £894

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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Packages with flights are ATOL protected

Top West Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,455, price is now £894 per person
£894
per person
3 Oct - 10 Oct
found 11 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Everyone there was friendly and gave us a lot of places to go eat for our one year anniversary

Reviewed on 21 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,643, price is now £1,044 per person
£1,044
per person
3 Oct - 10 Oct
found 11 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (654 reviews)
Loved everything about it. Amazing room, view and pool!

Reviewed on 20 Aug 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,875, price is now £1,232 per person
£1,232
per person
3 Oct - 10 Oct
found 11 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
Staff was amazing!! Everything was so easy checking in and checking out. The stay was great! It was so nice having the pier to ourselves after hours.

Reviewed on 20 Aug 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,663, price is now £1,115 per person
£1,115
per person
24 Oct - 31 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (277 reviews)
The staff were excellent

Reviewed on 21 Aug 2025

Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
Save 100% on your flight
Price was £1,723, price is now £1,158 per person
£1,158
per person
12 Oct - 19 Oct
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
7.6/10 Good! (1,000 reviews)
Hotel is beautiful and all of the staff is amazing. Only annoying thing is no free parking. Other than that amazing stay and happy we chose this hotel!

Reviewed on 18 Aug 2025

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

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 £154 per night from 1 Sept to 2 Sept
£154
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,392 reviews)
"Good experience with the staff"

Reviewed on 19 Aug 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 £141 per night from 2 Sept to 3 Sept
£141
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"It's not right downtown but close enough... a good little walk to here and there... not bad. I'd stay again if opportunity arises"

Reviewed on 19 Aug 2025

Holiday Inn & Suites Chicago - Downtown by IHG
Hyatt Place Chicago Medical/University District

Hyatt Place Chicago Medical/University District

3 out of 5
1835 W Harrison Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £119 per night from 1 Sept to 2 Sept
£119
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,264 reviews)
"United center"

Reviewed on 17 Aug 2025

Hyatt Place Chicago Medical/University District
See all 779 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

United Center

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
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

What to do in West Side

Urbana–Champaign Scavenger Hunt: Hunting Illini

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

£9
per adult
Self-Guided Illinois Scavenger Hunt: The Great Quest in Illinois
River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in West Side

Frequently asked questions

How much does a West Side travel package cost?
Starting from as low as £894, a package is your ticket to low-cost travel. Put together your West Side trip by selecting from our great range of airfares, hotels and rental cars.
If I'm not able to travel, can I cancel my West Side travel package?
Because we understand life can throw you a few curveballs, the answer is yes. For further information, visit our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change it for free. Your hotel, airline or car rental company may impose a fee if you made your booking a while ago.
How do I get a cheap travel package to West Side?
Just think of all the wonderful things you could do in West Side with a wad of extra cash in your wallet. Watch your savings stack up when you bundle your flights, hotels and extras into a West Side holiday package. You have loads of choice when you book your trip with Expedia too. In fact, you can select from more than 550 airlines and 1,000,000 hotel options around the globe. Whether you're enjoying a break with the whole family or going it alone, exploring West Side is better with a package.
Does Expedia offer Book Now, Pay Later West Side holidays?
Expedia has teamed up with online lender Klarna to make your next break a little easier on the wallet. Paying by instalment means you can spread the costs of your next dream escape, leaving you with more cash to play with while you're away. Klarna has several payment plans to choose from, so you're sure to find something that fits your budget. Browse these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month sounds right for you, Klarna can help. Paying in convenient monthly instalments will make that dream getaway possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay for your holiday in multiple transactions.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to click that "book now" button, opt for a low deposit holiday payment plan from Klarna.

How far in advance should I book my West Side holiday?
It's hard to pick the ideal time for airfares, but we generally suggest the earlier, the better. Plenty of international journeys on Expedia become available up to 12 months in advance. If you're unable to do so, don't fret. Discounted prices appear from time to time just weeks before departure dates.
What does an Expedia West Side travel package include?
You can choose from any combination of rental cars, hotels and flights. Once you've made your booking, you can add the fun stuff like experiences and tours. Want to pick your airfare class? That's possible too. The choice is all yours when it comes to crafting your dream West Side escape.
What should I know before booking a West Side travel package?
When you book your hotels, flights and car rentals together, you'll nab amazing discounts. Whether you're organising a beach escape in a villa or want to stay in a cosy apartment in the city, Expedia can make it happen for less.
Can I choose my airline with a West Side Expedia travel package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the flexibility to take your pick of available flights, hotels and activities that suit you.

* 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.