West Side Holidays from £1,140

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  • Better together

    Save up to £750 when you book a flight and hotel together*

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

  • Rest easy

    Packages with flights are ATOL protected

Top West Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was £1,561, price is now £1,140 per person
£1,140
per person
30 Sept - 5 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
The room was amazing! It was spacious and clean. The staff were helpful and very considerate. The hotel is located in an ideal location, right off of Michigan Avenue, in the heart of downtown. Shopping and restaurants are within short walking distances.

Reviewed on 8 Jul 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,035, price is now £1,325 per person
£1,325
per person
11 Sept - 16 Sept
found 9 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
Wonderful amenities, clean and great location. The only thing I did not care for was checking myself in. Front staff welcome you but you have to complete your own check in. After a long day if travel the last thing a person wants to do is complete forms. Lowers the Luxury feel of the property when the front desk does not do what an average Holiday Inn does.

Reviewed on 6 Jul 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £2,231, price is now £1,589 per person
£1,589
per person
30 Sept - 5 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)
Excellent service. Room was fantastic with an incredible view of the city. Definitely worth every penny! Will go back for sure!

Reviewed on 9 Jul 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was £1,696, price is now £1,242 per person
£1,242
per person
30 Sept - 5 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,886, price is now £1,384 per person
£1,384
per person
1 Oct - 6 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.

Reviewed on 8 Jul 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
A cityscape with modern skyscrapers and a curved highway.

West Loop

1 out of top 10 points of interest in this area

Consider a visit to The Old Post Office 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

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 refundableReserve now, pay when you stay
The price is £151 per night from 9 Aug to 10 Aug
£151
9 Aug - 10 Aug
includes taxes & fees
8.6/10 Excellent! (1,063 reviews)
"Everything was great. This was an overnight stay and this property exceeded my expectations."

Reviewed on 8 Jul 2026

Holiday Inn & Suites Chicago - Downtown by IHG
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 refundableReserve now, pay when you stay
The price is £180 per night from 9 Aug to 10 Aug
£180
9 Aug - 10 Aug
includes taxes & fees
9/10 Wonderful! (2,354 reviews)
"Place was nice and clean . I enjoyed my stay"

Reviewed on 9 Jul 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 £229 per night from 9 Aug to 10 Aug
£229
9 Aug - 10 Aug
includes taxes & fees
The Emily Hotel
See all 803 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

Stay near popular West Side attractions

A large, modern building with a curved facade and multiple vertical windows.

United Center

8.8/10 (4,269 reviews)
Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.
See properties

What to do in West Side

A Remarkable Scavenger Hunt: The Great Quest in Illinois

A Remarkable Scavenger Hunt: The Great Quest in Illinois

£9
per adult
A Remarkable Scavenger Hunt: The Great Quest in Illinois
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£19
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in West Side

Frequently asked questions

How much does a West Side travel package cost?
Starting from as low as £1,140, 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.

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. Flight-inclusive packages are ATOL protected.