Title: Luxury Vacations in West Side 2026 | Expedia.ca ![](https://images.trvl-media.com/place/829/ad657303-bbed-4f45-9ba5-b7c23d3e76f3.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # West Side Luxury Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by throwingsofas - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Flight and Luxury hotel deals in West Side Price found within the past 48 hours. Click for updated prices. ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $817 per person May 7 - May 10 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,140 reviews) The hotel itself is beautiful, the lounge and bar area are so cozy and the cocktails are amazing! The entire staff is friendly and welcoming. Our stay at The Pendry was great! Shout out to our friend Anis at the bar lounge for his excellent hospitality. Reviewed on Apr 4, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,216 per person Jun 19 - Jun 22 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Beautiful rooms at an amazing location. Parking is terribly expensive though, and breakfast is not included. There is no mini fridge, so good luck saving leftovers to reduce expenses. There is also no swimming pool which I found weird for a place this elegant. Their main restaurant does not have good breakfast. Go for dinner or lunch and you will be very happy. But don't bother with breakfast, it's just a bunch of cheese and grease and it's unpleasant. Reviewed on Apr 4, 2026 ![Le Méridien Essex Chicago](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/f13a5c54_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Le Méridien Essex Chicago Downtown Chicago CA $1,111 per person Jun 19 - Jun 22 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 8.8/10 Excellent! (1,012 reviews) Le Meridien Exxex Chicago is in the perfect location, steps from where I need to be when visiting Chicago. The staff are super helpful and friendly. The restaurant serves delicious food and the waitstaff is attentive. Keep up the good work! Reviewed on Apr 3, 2026 ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/8bd99f5f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Chicago at Millennium Park Downtown Chicago CA $943 per person Jun 19 - Jun 22 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 8.6/10 Excellent! (2,076 reviews) Everything was perfect Reviewed on Mar 26, 2026 ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $1,477 per person Jun 19 - Jun 22 found 1 day ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Best free Hotel breakfast you will ever have Reviewed on Apr 4, 2026 Don't see what you're looking for? See all available trips from Columbus to West Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-05/2026-05-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Luxury holidays in West Side Price found within the past 48 hours. Click for updated prices. ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago CA $1,266 per person May 23 - May 26 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,005 reviews) Great location and property Reviewed on Mar 14, 2026 ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1ede47da_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,503 per person May 23 - May 26 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,007 reviews) Great place to stay . The staff was friendly and helpful !!! Reviewed on Mar 22, 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,868 per person Jun 19 - Jun 22 found 1 day ago Roundtrip flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (1,852 reviews) Highly recommend a stay here! The staff are amazing and the restaurant is incredible; get the French toast. Reviewed on Apr 4, 2026 Don't see what you're looking for? See all available trips from Columbus to West Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-05/2026-05-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Luxury holidays in West Side Price found within the past 48 hours. Click for updated prices. ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $817 per person May 7 - May 10 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,140 reviews) The hotel itself is beautiful, the lounge and bar area are so cozy and the cocktails are amazing! The entire staff is friendly and welcoming. Our stay at The Pendry was great! Shout out to our friend Anis at the bar lounge for his excellent hospitality. Reviewed on Apr 4, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,216 per person Jun 19 - Jun 22 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Beautiful rooms at an amazing location. Parking is terribly expensive though, and breakfast is not included. There is no mini fridge, so good luck saving leftovers to reduce expenses. There is also no swimming pool which I found weird for a place this elegant. Their main restaurant does not have good breakfast. Go for dinner or lunch and you will be very happy. But don't bother with breakfast, it's just a bunch of cheese and grease and it's unpleasant. Reviewed on Apr 4, 2026 ![Le Méridien Essex Chicago](https://images.trvl-media.com/lodging/36000000/35140000/35130400/35130365/f13a5c54_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Le Méridien Essex Chicago Downtown Chicago CA $1,111 per person Jun 19 - Jun 22 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Chicago (ORD) 8.8/10 Excellent! (1,012 reviews) Le Meridien Exxex Chicago is in the perfect location, steps from where I need to be when visiting Chicago. The staff are super helpful and friendly. The restaurant serves delicious food and the waitstaff is attentive. Keep up the good work! Reviewed on Apr 3, 2026 Don't see what you're looking for? See all available trips from Columbus to West Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-05/2026-05-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Luxury holidays in West Side Price found within the past 48 hours. Click for updated prices. ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $1,024 per person Jun 22 - Jun 26 found 1 hour ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Best free Hotel breakfast you will ever have Reviewed on Apr 4, 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $1,090 per person Jun 22 - Jun 26 found 1 hour ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) Was a little noisy but I think that was just my unit. Facilities were top notch! Reviewed on Apr 4, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,307 per person May 25 - May 29 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Beautiful rooms at an amazing location. Parking is terribly expensive though, and breakfast is not included. There is no mini fridge, so good luck saving leftovers to reduce expenses. There is also no swimming pool which I found weird for a place this elegant. Their main restaurant does not have good breakfast. Go for dinner or lunch and you will be very happy. But don't bother with breakfast, it's just a bunch of cheese and grease and it's unpleasant. Reviewed on Apr 4, 2026 Don't see what you're looking for? See all available trips from Columbus to West Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-05-05/2026-05-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the perfect luxury West Side vacation with Expedia #### What are some benefits when booking luxury West Side vacations? When you book a luxury West Side vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax. #### How can I find all-inclusive luxury vacations in West Side? If you're looking for something luxurious in West Side, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together. #### Can I book a cheap luxury vacation? While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $817, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 29\. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first. #### Are there luxury spa vacations? Yes, luxury spa vacations are available and quite popular in West Side. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search. #### What should I look for in a luxury family vacation in West Side? When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout West Side. #### Can I book last-minute luxury vacations? Yes, last-minute bookings are often available in West Side. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces. #### What can help me find the best luxury vacation deals in West Side? You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of West Side or travelling to more obscure destinations altogether can often lead to lower prices. #### Can I book a luxury vacation that is fully refundable? Yes, fully refundable reservations are sometimes available on luxury vacation packages in West Side. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking. #### Why should I book my luxury vacation with Expedia? When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Top Luxury Vacation Destinations > - [Luxury vacations in India ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/80/India) > - [Luxury vacations in France ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/59/France) > - [Luxury vacations in Switzerland ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/174/Switzerland) > - [Luxury vacations in Canada ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/31/Canada) > - [Luxury vacations in Jamaica ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/88/Jamaica) > - [Luxury vacations in Italy ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/86/Italy) > - [Luxury vacations in New Zealand ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/133/New-Zealand) > - [Luxury vacations in the Maldives ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/109/Maldives) > - [Luxury vacations in Costa Rica ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/42/Costa-Rica) > - [Luxury vacations in Florida Keys ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6023765/Florida-Keys) > - [Luxury vacations in Mexico ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/117/Mexico) > - [Luxury vacations in the Caribbean ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6022969/Caribbean) > - [Luxury vacations in Zanzibar ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/4186/Zanzibar) > - [Luxury vacations in Cancun ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/179995/Cancun) > - [Luxury vacations in Kerala ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/602187/Kerala) > - [Luxury vacations in Australia ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/10/Australia) > - [Luxury vacations in Puglia ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/6048562/Puglia) > - [Luxury vacations in Cuba ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/44/Cuba) > - [Luxury vacations in Cyprus ](https://www.expedia.ca/lp/theme-vacations/luxury-vacations/45/Cyprus) ## More Vacations Ideas [Flights to West Side ](https://expedia.ca/Cheap-Flights-To-West-Side.d553248635976475400.Travel-Guide-Flights)[ West Side Hotels ](https://expedia.ca/West-Side-Hotels.d553248635976475400.Travel-Guide-Hotels)[ West Side Vacation Rentals ](https://expedia.ca/West-Side-Vacation-Rentals.d553248635976475400.Travel-Guide-VacationRentals)[ West Side Car Rentals ](https://expedia.ca/Car-Rentals-In-West-Side.d553248635976475400.Car-Rental-Guide)[ West Side Vacations ](https://expedia.ca/West-Side.d553248635976475400.Destination-Travel-Guides)[ Things to do in West Side ](https://expedia.ca/Things-To-Do-In-West-Side.d553248635976475400.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app