West Side Holidays from £1,105
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Top West Side Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown
Downtown Chicago
£2,221
per person
8 Oct - 15 Oct
found 22 hours ago
Return direct flight included
Leeds (LBA) to Chicago (ORD)
9.2/10 Wonderful! (2,348 reviews)
We came down for one night and this hotel did just what it needed to know at a great price!
Reviewed on 23 Aug 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
£2,034
per person
8 Oct - 15 Oct
found 22 hours ago
Return direct flight included
Leeds (LBA) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
I absolutely loved my stay. It was in the perfect location. Walking distance to every site to see. Their customer customer service was great. As well as the in house dining. I definitely will stay here again the next time I visit Chicago
Reviewed on 22 Aug 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
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.
West Town
2 out of top 10 points of interest in this area
Noted for its live music and theatres, there's plenty to explore in West Town. Top attractions like The Salt Shed and Milwaukee Avenue are major draws, and you can hop on the metro at Division Station or Damen Station to see more of the city.
Near West Side
4 out of top 10 points of interest in this area
Live music, theatres and shopping highlight some notable features of Near West Side. Make a stop by United Center or Credit Union 1 Arena while you're visiting, and jump aboard the metro at Polk Station (Pink Line) or Racine Station to get around town.
Wicker Park
Spend some time visiting places like Milwaukee Avenue while getting to know Wicker Park, and be sure to check out the abundant dining options. You can hop aboard the metro at Damen Station or Division Station to see more of the area.
West Loop Gate
While you're in West Loop Gate, take in top sights like Cobra Lounge or Old St Patrick’s Church, and hop on the metro to see more of the city at Ogilvie Transportation Center or Clinton Station (Green Line).
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
25 South Halsted Street Chicago IL
Fully refundable
£150
30 Aug - 31 Aug
includes taxes & fees
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
Fully refundable
£139
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (1,182 reviews)
"The room was not clean the carpet was frayed and dirty. The bathroom smelled like it had not been mopped in months.The windows had spiderwebs and dust. The iron did not work. The pool had unkept furniture and a bees nest along the railings. The outside of the hotel had trash surrounding it and homeless ..."
Reviewed on 23 Aug 2026
The Emily Hotel
311 North Morgan Street Chicago IL
Fully refundableReserve now, pay when you stay
£227
30 Aug - 31 Aug
includes taxes & fees
9.2/10 Wonderful! (1,345 reviews)
"Overall our room felt cheap. Biggest complaint was how loud the room was. Little to no soundproofing it seemed like. Hotel also let multiple cars sit in valet for 10+ minutes with music blaring. Wouldn't stay here again."
Reviewed on 23 Aug 2026
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.
Stay near popular West Side attractions
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 fascinating museums.
University of Illinois Chicago
8.4/10 (1,058 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.
Humboldt Park
7.0/10 (2 reviews)
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 theatre scene and fascinating museums in this vibrant area.
Garfield Park Conservatory
9.0/10 (6 reviews)
While away the afternoon in this huge conservatory housing tropical and rare plants, waterfalls and art.
Credit Union 1 Arena
8.0/10 (5 reviews)
Catch an event at Credit Union 1 Arena during your trip to Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
The Salt Shed
You can get tickets for a performance at The Salt Shed on your trip to Chicago. Experience the live music and theatre scene in this vibrant area.
Anna and Frederick Douglass Park
7.0/10 (12 reviews)
After visiting Anna and Frederick Douglass Park, make a plan to see the other sights and activities in Chicago. Experience the fascinating museums and acclaimed art galleries in this vibrant area.
Union Park
After visiting Union Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the acclaimed theatre scene in this vibrant area.
What to do in West Side
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
90% of travellers recommend
Frequently asked questions
How much does a West Side travel package cost?
Starting from as low as £1,105, 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
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- West Loop Hotels
- B&B in West Side
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- Flights to Chicago
- American Airlines Dublin (DUB) to Chicago (ORD) flights
- British Airways London (LHR) to Chicago (ORD) flights
- Flights from Chicago
- Flights from Columbus (CMH) to Chicago (ORD)
- Flights from Dublin (DUB) to Chicago (ORD)
- Flights from Edinburgh (EDI) to Chicago (ORD)
- Flights from Glasgow (GLA) to Chicago (ORD)
- Flights from London (LGW) to Chicago (ORD)
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- Flights from Tulsa (TUL) to Chicago (ORD)
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- Art Institute of Chicago
- Visit Downtown Chicago
- Chicago Harbor Lighthouse
- Visit Humboldt Park
- Visit Little Village
- Visit Magnificent Mile
- Visit Printers Row
- Chicago Riverwalk
- Visit The Loop
- Chicago Theatre
- Chicago Water Tower
- Chicago Holidays
- Visit Chicago
- Cibc Theatre
- Cicero Holidays
- Downtown Chicago Holidays
- Ernest Hemingway Museum and House
- Garfield Park Conservatory
- Grant Park
- Hillside Holidays
- Lakeview Holidays
- Lincoln Hall
- Lincoln Park Conservatory
- Lincoln Park Zoo
- Lincoln Park Holidays
- Michigan Avenue
- Millennium Park
- Montrose Beach
- Navy Pier
- Northwestern University
- Visit Oak Park
- Robie House
- Shops at North Bridge
- The Loop Holidays
- Unity Temple
- Willis Tower
- Wrigley Field
* 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.
