Title: Beach Vacations in Chicago 2026 | Expedia.ca ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chicago 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 Chicago Price found within the past 48 hours. Click for updated prices. ![Hotel Lincoln](https://images.trvl-media.com/lodging/1000000/30000/23400/23314/48b7272b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Lincoln Lincoln Park CA $494 per person Feb 19 - Feb 22 found 3 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Chicago (ORD) 7.8/10 Good! (1,050 reviews) Staff was very welcoming. The room was above my expectations. A lot of room, clean, and comfortable. Reviewed on Dec 19, 2025 ![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 $591 per person Mar 16 - Mar 19 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Chicago (ORD) 7.6/10 Good! (1,001 reviews) Clean room, good service and great area. Reviewed on Dec 18, 2025 ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/7e178380_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Chicago at Millennium Park Downtown Chicago CA $653 per person Jan 20 - Jan 23 found 6 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 8.6/10 Excellent! (2,022 reviews) My family and I stayed in a one bedroom suite with gold lounge access for the weekend, and had a really wonderful experience! We stayed in a beautifully renovated room with a lovely view. However, the real wow factor was in the exceptional service! Mandana and the other staff in the gold lounge were really wonderful! My husband left his expensive and favorite dress shoes in the suite, and he didn't realize until 2 days after we checked out. Within 5 minutes of my husband's call to Security, they checked the suite which had yet to be cleaned, and notified my husband that they had located his shoes. We will definitely be back! Reviewed on Dec 19, 2025 ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars Magnificent Mile Downtown Chicago CA $711 per person Feb 22 - Feb 27 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Chicago (ORD) 8.8/10 Excellent! (3,098 reviews) The staff were great. However, the room shook whenever someone closed a door to another room in the hall. This made it hard to get a good sleep. Their choice of toilet tissue was surprisingly cheap. Single ply TP is something you use if there’s no other option, not in a decent hotel in a major city center. Reviewed on Dec 19, 2025 ![Thompson Chicago, by Hyatt](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/w2559h3837x0y3-191558cd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Thompson Chicago, by Hyatt Downtown Chicago CA $544 per person Jan 21 - Jan 24 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,266 reviews) I stayed at the Thompson in Nashville and it was GORGEOUS. I expected the same here but was slightly disappointed. The rooms seemed dated. The shower in the bathroom was leaking to other parts of the background. I could hear all the traffic noise from the street despite being on the 7th floor. Would I stay here again? Probably not. Not for the money. Reviewed on Dec 18, 2025 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Beach holidays in Chicago Price found within the past 48 hours. Click for updated prices. ![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 $1,682 per person Feb 11 - Feb 15 found 13 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.2/10 Wonderful! (1,004 reviews) The room was spotless and the bed super comfy. The staff was very helpful and extremely courteous. Reviewed on Dec 15, 2025 ![Four Seasons Hotel Chicago](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/7da48e89_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Four Seasons Hotel Chicago Downtown Chicago CA $2,121 per person Feb 25 - Mar 1 found 16 hours ago Roundtrip non-stop flight included St. John's (YYT) to Chicago (ORD) 9.4/10 Exceptional! (999 reviews) Very nice amenities and wellness facility. High end shopping within a very short walk. Reviewed on Dec 16, 2025 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Beach holidays in Chicago 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 $591 per person Mar 16 - Mar 19 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Chicago (ORD) 7.6/10 Good! (1,001 reviews) Clean room, good service and great area. Reviewed on Dec 18, 2025 ![Fairmont Chicago at Millennium Park](https://images.trvl-media.com/lodging/1000000/20000/16000/15937/7e178380_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fairmont Chicago at Millennium Park Downtown Chicago CA $653 per person Jan 20 - Jan 23 found 6 hours ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 8.6/10 Excellent! (2,022 reviews) My family and I stayed in a one bedroom suite with gold lounge access for the weekend, and had a really wonderful experience! We stayed in a beautifully renovated room with a lovely view. However, the real wow factor was in the exceptional service! Mandana and the other staff in the gold lounge were really wonderful! My husband left his expensive and favorite dress shoes in the suite, and he didn't realize until 2 days after we checked out. Within 5 minutes of my husband's call to Security, they checked the suite which had yet to be cleaned, and notified my husband that they had located his shoes. We will definitely be back! Reviewed on Dec 19, 2025 ![The Drake](https://images.trvl-media.com/lodging/1000000/20000/15100/15092/w3840h2550x0y3-037e0eb4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Drake Downtown Chicago CA $628 per person Feb 13 - Feb 16 found 20 hours ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 8.8/10 Excellent! (1,369 reviews) This time the room was great. Reviewed on Dec 19, 2025 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Beach holidays in Chicago Price found within the past 48 hours. Click for updated prices. ![Thompson Chicago, by Hyatt](https://images.trvl-media.com/lodging/1000000/30000/26100/26076/w2559h3837x0y3-191558cd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Thompson Chicago, by Hyatt Downtown Chicago CA $766 per person Feb 11 - Feb 15 found 16 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.2/10 Wonderful! (1,266 reviews) I stayed at the Thompson in Nashville and it was GORGEOUS. I expected the same here but was slightly disappointed. The rooms seemed dated. The shower in the bathroom was leaking to other parts of the background. I could hear all the traffic noise from the street despite being on the 7th floor. Would I stay here again? Probably not. Not for the money. Reviewed on Dec 18, 2025 ![Swissotel - Chicago](https://images.trvl-media.com/lodging/1000000/20000/17300/17288/7af111e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Swissotel - Chicago Downtown Chicago CA $856 per person Feb 11 - Feb 15 found 13 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9/10 Wonderful! (2,947 reviews) Wonderful. It’s just an overnight stay but the staff is exceptional Reviewed on Dec 19, 2025 ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Regency Chicago Downtown Chicago CA $921 per person Feb 11 - Feb 15 found 13 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (3,386 reviews) From beginning to end it was awesome.....Except for parking it was horrible I got lost for about 30 mins trying to find my rental....BUT the 🏨 employees were all very helpful and we found it in no time after that ❤️.....The 🏨 was awesome, views ❤️ and the vibe was on point everything was at a walking distance 🥰.... Beautiful city day or 🌃 please preserve it as much as you can. I'm from California and greatly appreciate the hospitality ❤️ 🙏 Reviewed on Dec 18, 2025 Don't see what you're looking for? See all available trips from Columbus to Chicago [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Find the best beach vacations in Chicago #### What are some benefits when booking beach vacations in Chicago? When you travel to the beach in Chicago, 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 Chicago? 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 Chicago 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 Chicago? There are quite a few things you can do to get cheap beach vacations in Chicago. Prices range from CA $494, 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 Chicago. These package deals let you save by booking your accommodation and your flight together with savings of up to 17\. #### Why should I book family beach vacations? When you're travelling with the family to Chicago, 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 Chicago? It's easy to find a beachfront vacation accommodation in Chicago 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 Chicago 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 Chicago 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 Illinois. 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 Chicago ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago/Magnificent Mile Suites 198 E Delaware Pl Chicago IL - 11 min walk from Michigan Avenue Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ... 8.8/10 Excellent! (3,498 reviews) Great location! Nice view, good staff Reviewed on Dec 17, 2025 [](https://expedia.ca/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Eurostars Magnificent Mile 660 North State Street Chicago IL - 5 min walk from Michigan Avenue Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms ... 8.8/10 Excellent! (3,149 reviews) The staff were great. However, the room shook whenever someone closed a door to another room in the hall. This made it hard to get a good sleep. Their choice of toilet tissue was surprisingly cheap. Single ply TP is something you use if there’s no other option, not in a decent hotel in a major city ... Reviewed on Dec 19, 2025 [](https://expedia.ca/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Silversmith Hotel Chicago Downtown 10 S Wabash Ave Chicago IL - 14 min walk from Michigan Avenue Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ... 9.2/10 Wonderful! (2,120 reviews) Beautiful old hotel convenient to downtown . Wonderful rooms and great onsite dining. You can hear the trains outside from pretty much every room but I found it acceptable noise level. Reviewed on Dec 13, 2025 [](https://expedia.ca/Chicago-Hotels-Silversmith-Hotel-Chicago-Downtown.h116674.Hotel-Information) [See all 5,624 properties in Chicago](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=178248) 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 Chicago ](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[ Chicago Hotels ](https://expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels)[ Chicago Vacation Rentals ](https://expedia.ca/Chicago-Vacation-Rentals.d178248.Travel-Guide-VacationRentals)[ Chicago Car Rentals ](https://expedia.ca/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide)[ Chicago Vacations ](https://expedia.ca/Chicago.d178248.Destination-Travel-Guides)[ Things to do in Chicago ](https://expedia.ca/Things-To-Do-In-Chicago.d178248.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