Title: Beach Vacations in Northwest Side 2026 | Expedia.ca ![](https://images.trvl-media.com/place/829/2253d64b-0974-4770-85a9-32842b88f38f.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Northwest Side Beach Vacations ## Book a Hotel + Flight or Car together to unlock savings - ## 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 Beach hotel deals in Northwest Side Price found within the past 48 hours. Click for updated prices. ![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Orrington / Evanston Downtown Evanston CA $507 per person Feb 17 - Feb 21 found 19 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 7.6/10 Good! (1,002 reviews) Clean rooms, great location in Evanston near the university. Helpful staff. Reviewed on Nov 17, 2025 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $1,902 per person Jan 31 - Feb 6 found 22 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing Reviewed on Dec 16, 2025 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $808 per person Jan 31 - Feb 6 found 22 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside Reviewed on Dec 4, 2025 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $988 per person Feb 23 - Feb 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom. Reviewed on Dec 14, 2025 ![Radisson Blu Aqua Hotel Chicago](https://images.trvl-media.com/lodging/5000000/4530000/4520700/4520626/8cd3425b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Radisson Blu Aqua Hotel Chicago Downtown Chicago CA $725 per person Jan 31 - Feb 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 8.6/10 Excellent! (1,761 reviews) Hotel was amazing all around! Friendly and very helpful staff. Clean rooms and a Starbucks! Reviewed on Dec 14, 2025 Don't see what you're looking for? See all available trips from Columbus to Northwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Beach holidays in Northwest Side Price found within the past 48 hours. Click for updated prices. ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $988 per person Feb 23 - Feb 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom. Reviewed on Dec 14, 2025 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $1,902 per person Jan 31 - Feb 6 found 22 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing Reviewed on Dec 16, 2025 ![The Ritz-Carlton, Chicago](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/30b68b68_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton, Chicago Downtown Chicago CA $1,825 per person Jan 31 - Feb 6 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,002 reviews) The room was spotless and the bed super comfy. The staff was very helpful and extremely courteous. Reviewed on Dec 15, 2025 Don't see what you're looking for? See all available trips from Columbus to Northwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Beach holidays in Northwest 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 $520 per person Feb 18 - Feb 21 found 18 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Room was spotless & staff were courteous Reviewed on Dec 16, 2025 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,117 per person Mar 12 - Mar 15 found 23 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom. Reviewed on Dec 14, 2025 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $1,313 per person Mar 12 - Mar 15 found 23 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing Reviewed on Dec 16, 2025 Don't see what you're looking for? See all available trips from Columbus to Northwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Beach holidays in Northwest Side Price found within the past 48 hours. Click for updated prices. ![Hyatt Place Chicago/ Schaumburg](https://images.trvl-media.com/lodging/1000000/90000/82300/82257/df623816_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Place Chicago/ Schaumburg CA $469 per person Feb 12 - Feb 16 found 1 hour ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.6/10 Excellent! (1,000 reviews) Friendly staff, nice workout room, great breakfast. Reviewed on Dec 14, 2025 ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $548 per person Feb 23 - Feb 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff. Reviewed on Dec 8, 2025 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $988 per person Feb 23 - Feb 27 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom. Reviewed on Dec 14, 2025 Don't see what you're looking for? See all available trips from Columbus to Northwest Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-24/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find the best beach vacations in Northwest Side #### What are some benefits when booking beach vacations in Northwest Side? When you travel to the beach in Northwest Side, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip. #### How can I book the best beach vacations in Northwest Side? To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Northwest Side trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit. #### Can I book cheap beach vacations in Northwest Side? There are quite a few things you can do to get cheap beach vacations in Northwest Side. Prices range from CA $469, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out. #### Can I book beach packages? Yes, and you'll find quite a few beach packages available in Northwest Side. These package deals let you save by booking your accommodation and your flight together with savings of up to 30\. #### Why should I book family beach vacations? When you're travelling with the family to Northwest Side, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room. #### How can I find a beachfront vacation in Northwest Side? It's easy to find a beachfront vacation accommodation in Northwest Side using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline. #### How can I book last-minute beach vacations? Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Northwest Side as your destination and see what's available. #### Can I find all-inclusive beach vacations ? Yes, all you have to do to find all-inclusive beach vacations in Northwest Side is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance. #### Can I book a beach trip that's fully refundable? Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Chicago. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too. #### Why should I book beach vacations with Expedia? When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips. ## Beach Hotels in Northwest Side ![Luxe Duplex - Private Gym -Huge Yard -King Beds Garage Parking-EV Charger- Crib](https://images.trvl-media.com/lodging/90000000/89850000/89845700/89845610/5a36511c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Luxe Duplex - Private Gym -Huge Yard -King Beds Garage Parking-EV Charger- Crib Chicago IL - 8 min drive from Walt Disney House Book a stay at this family-friendly vacation home in Chicago. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Portage Park and Copernicus ... 9.2/10 Wonderful! (19 reviews) The easter eggs of amenities. Every time we looked around we saw many new amenities. We enjoyed the gym, and prompt service requests. Everything was clean. Having a suggestion box was awesome. Great stay comfortable beds. Reviewed on Nov 12, 2025 [](https://expedia.ca/Chicago-Hotels-Luxurious-Modern-Home-W-Private-Gym.h89845610.Hotel-Information) ![Historic 1920s Private Bungalow Near Logan Square! ](https://images.trvl-media.com/lodging/20000000/19190000/19187600/19187552/b7361c79_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Historic 1920s Private Bungalow Near Logan Square! Chicago IL - 19 min walk from Walt Disney House Book a stay at this family-friendly vacation home in Chicago. Enjoy a water park, a garden, and laundry facilities. Popular attractions Wrigley Field and United ... 9.8/10 Exceptional! (39 reviews) Superb host and excellent accommodations. Can't get better than this experience. Reviewed on Oct 13, 2025 [](https://expedia.ca/Chicago-Hotels-Historic-1920s-Private-Bungalow-Near-Logan-Square.h19187552.Hotel-Information) ![Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square](https://images.trvl-media.com/lodging/100000000/99400000/99394200/99394128/w1433h1080x244y0-98db7321_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square Chicago IL - 3 min walk from Walt Disney House Book a stay at this family-friendly vacation home in Chicago. Enjoy free WiFi, a garden, and patios. Popular attractions United Center and Wrigley Field are ... 9.8/10 Exceptional! (13 reviews) House was great very quiet and clean Reviewed on Jul 26, 2025 [](https://expedia.ca/Chicago-Hotels-Hermosa-House-ECO-HOME-Quiet.h99394128.Hotel-Information) [See all 5,121 properties in Northwest Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248635976475367) 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. ## 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 Beach Vacation Destinations > - [Myrtle beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/601685/Myrtle-Beach) > - [Miami beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/8833/Miami-Beach) > - [Florida beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/211/Florida) > - [Barbados beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/16/Barbados) > - [South beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6138745/South-Beach) > - [Palm beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/9061/Palm-Beach) > - [Daytona beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6023995/Daytona-Beach) > - [Newport beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/8111/Newport-Beach) > - [Vero beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6023660/Vero-Beach) > - [India beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/80/India) > - [Laguna beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/6298668/Laguna-Beach) > - [Ontario beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/2680/Ontario) > - [Canada beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/31/Canada) > - [Barcelona beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/179992/Barcelona) > - [Fort Myers beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/7194/Fort-Myers-Beach) > - [Portugal beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/147/Portugal) > - [Italy beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/86/Italy) > - [Thailand beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/178/Thailand) > - [France beach vacations ](https://www.expedia.ca/lp/theme-vacations/beach-vacations/59/France) ## More Vacations Ideas [Flights to Northwest Side ](https://expedia.ca/Cheap-Flights-To-Northwest-Side.d553248635976475367.Travel-Guide-Flights)[ Northwest Side Hotels ](https://expedia.ca/Northwest-Side-Hotels.d553248635976475367.Travel-Guide-Hotels)[ Northwest Side Vacation Rentals ](https://expedia.ca/Northwest-Side-Vacation-Rentals.d553248635976475367.Travel-Guide-VacationRentals)[ Northwest Side Car Rentals ](https://expedia.ca/Car-Rentals-In-Northwest-Side.d553248635976475367.Car-Rental-Guide)[ Northwest Side Vacations ](https://expedia.ca/Northwest-Side.d553248635976475367.Destination-Travel-Guides) \* 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