West Side Holidays from £944
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Top West Side Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
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 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.
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.
Humboldt Park
While Humboldt Park isn't home to many top sights, Garfield Park Conservatory and National Museum of Puerto Rican Arts & Culture are some notable places to visit nearby.
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
506 West Harrison Street Chicago IL
Fully refundable
£146
1 Nov - 2 Nov
includes taxes & fees
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
Fully refundable
£137
8 Nov - 9 Nov
includes taxes & fees
The Emily Hotel
311 North Morgan Street Chicago IL
Fully refundableReserve now, pay when you stay
£148
1 Nov - 2 Nov
includes taxes & fees
9.2/10 Wonderful! (1,344 reviews)
"Unique stay and fun location. Staff was thoughtful."
Reviewed on 8 Oct 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 acclaimed theatre scene.
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 fascinating museums 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 fascinating museums and acclaimed art galleries in this vibrant area.
Garfield Park
After visiting Garfield Park, make a plan to see the other sights and activities in Chicago. Discover the top-notch restaurants and acclaimed 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 acclaimed theatre scene and fascinating museums 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.
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 entertainment choices in this vibrant area.
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.
What to do in West Side
Skydeck Chicago at Willis Tower
£32
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% of travellers recommend
Frequently asked questions
How much does a West Side travel package cost?
Starting from as low as £944, 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
- 5 Star Hotels in Chicago
- Serviced Apartments in Chicago
- Sports Hotels in Chicago
- All-Inclusive Hotels in Chicago
- Beach Resorts & in Chicago
- Boutique Hotels in Chicago
- Cheap Hotels in Chicago
- Casino Hotels in Chicago
- Family-Friendly Hotels in Chicago
- Hotels Suites in Chicago
- Hotels with Parking in Chicago
- Hotels with Parking in Chicago
- Hotels with Balcony in Chicago
- Hotels with Hot Tubs in Chicago
- Hotels with Pool in Chicago
- Lakeside Hotels in Chicago
- Luxury Hotels in Chicago
- Pet-Friendly Hotels in Chicago
- Riverside Hotels in Chicago
- Romantic Hotels in Chicago
- Spa Hotels in Chicago
- Chicago Hotels
- Hotels near Chicago Union Station
- Cicero Hotels
- Hotels with a View in Downtown Chicago
- Downtown Chicago Hotels
- Hotels near Grant Park
- Little Village Hotels
- Logan Square Hotels
- Lower West Side Hotels
- Magnificent Mile Hotels
- Hotels near McCormick Place
- Hotels near Michigan Avenue
- Near West Side Hotels
- North Lawndale Hotels
- Hotels near Northwestern Memorial Hospital
- Hotels near Ogilvie Transportation Center
- River North Hotels
- The Loop Hotels
- Hotels near United Center
- West Loop Hotels
- B&B in West Side
- Wicker Park Hotels
- Hotels near Willis Tower
- 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)
- Flights from London (LHR) to Chicago (ORD)
- Flights from Manchester (MAN) to Chicago (ORD)
- Flights from Tulsa (TUL) to Chicago (ORD)
- Flights from Toronto (YYZ) to Chicago (ORD)
- 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.
