Title: Best Cottages in Chicago in 2026 | Expedia.co.uk [Chicago Travel Guide](https://expedia.co.uk/Chicago.dx178248)[Hotels in Chicago](https://expedia.co.uk/Chicago-Hotels.d178248.Travel-Guide-Hotels)[Holiday Rentals in Chicago](https://expedia.co.uk/Chicago-Holiday-Rentals.d178248.Travel-Guide-HolidayRentals)[Flights to Chicago](https://expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.co.uk/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Chicago Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chicago.d178248.Car-Hire-Guide)[Chicago Holidays](https://expedia.co.uk/Chicago.d178248.Holidays-City-Breaks) ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [20 Feb - 22 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=178248&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [3 Apr - 5 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=178248&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [1 May - 3 May](https://www.expedia.co.uk/Hotel-Search?regionId=178248&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [29 May - 31 May](https://www.expedia.co.uk/Hotel-Search?regionId=178248&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chicago cottages ![Exterior](https://images.trvl-media.com/lodging/120000000/119610000/119600300/119600217/ce22b04a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119610000/119600300/119600217/e8214cc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119610000/119600300/119600217/1e6ca342.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119610000/119600300/119600217/10f8d436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Pleasant Hill Cottage-Storybook Luxury Near Lake Michigan & Heart Of It All! [](https://www.expedia.co.uk/Chicago-Hotels-The-Pleasant-Hill-Cottage-Storybook-Luxury-Near-Lake-Michigan-Heart-Of-It-All.h119600217.Hotel-Information) Highwood £909 includes taxes & fees 10 Feb - 11 Feb [](https://www.expedia.co.uk/Chicago-Hotels-The-Pleasant-Hill-Cottage-Storybook-Luxury-Near-Lake-Michigan-Heart-Of-It-All.h119600217.Hotel-Information) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/101000000/100470000/100464000/100463970/440f1a78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/101000000/100470000/100464000/100463970/45962439.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/101000000/100470000/100464000/100463970/ceb6165b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/101000000/100470000/100464000/100463970/e8906bbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salem Vacation Home w/ Dock: Steps to Paddock Lake [](https://www.expedia.co.uk/Salem-Hotels-Salem-Vacation-Home-W-Dock-Steps-To-Paddock-Lake.h100463970.Hotel-Information) Salem £478 includes taxes & fees 8 Mar - 9 Mar [](https://www.expedia.co.uk/Salem-Hotels-Salem-Vacation-Home-W-Dock-Steps-To-Paddock-Lake.h100463970.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76720000/76715400/76715317/d129dbbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/77000000/76720000/76715400/76715317/267192e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76720000/76715400/76715317/2f366504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76720000/76715400/76715317/5d07dc35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Little Fox Cottage - A Cozy Riverview Getaway [](https://www.expedia.co.uk/Fox-River-Grove-Hotels-Little-Fox-Cottage-A-Cozy-Riverview-Getaway.h76715317.Hotel-Information) Fox River Grove 10/10 Exceptional (17 reviews) "Cute and efficient house to stay. Communication was perfect. The property had everything we needed including walking distance to the Ski Lodge. Would definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Antje K. £158 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Fox-River-Grove-Hotels-Little-Fox-Cottage-A-Cozy-Riverview-Getaway.h76715317.Hotel-Information) 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. [View all properties](https://expedia.co.uk/Hotel-Search?startDate=2026-02-21&endDate=2026-02-22®ionId=178248&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Chicago+%28and+vicinity%29%2C+Illinois%2C+United+States+of+America®ionId=178248&latLong=41.88078%2C-87.62813&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=APART_HOTEL) Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Chicago+%28and+vicinity%29%2C+Illinois%2C+United+States+of+America®ionId=178248&latLong=41.88078%2C-87.62813&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CABIN) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Chicago+%28and+vicinity%29%2C+Illinois%2C+United+States+of+America®ionId=178248&latLong=41.88078%2C-87.62813&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=APARTMENT) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Chicago+%28and+vicinity%29%2C+Illinois%2C+United+States+of+America®ionId=178248&latLong=41.88078%2C-87.62813&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VACATION_HOME) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Chicago+%28and+vicinity%29%2C+Illinois%2C+United+States+of+America®ionId=178248&latLong=41.88078%2C-87.62813&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=CONDO) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Chicago+%28and+vicinity%29%2C+Illinois%2C+United+States+of+America®ionId=178248&latLong=41.88078%2C-87.62813&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=VILLA) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Chicago+%28and+vicinity%29%2C+Illinois%2C+United+States+of+America®ionId=178248&latLong=41.88078%2C-87.62813&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=COTTAGE) Residences [](https://www.expedia.co.uk/Hotel-Search?destination=Chicago+%28and+vicinity%29%2C+Illinois%2C+United+States+of+America®ionId=178248&latLong=41.88078%2C-87.62813&adults=2&startDate=2026-05-08&d1=2026-05-08&endDate=2026-05-11&d2=2026-05-11&lodging=RESIDENCE) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChicago-Cottages.d178248-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChicago-Cottages.d178248-aaCottages.Travel-Guide-Accommodation) ## Top Chicago Hotel Reviews ![DoubleTree by Hilton Chicago - Magnificent Mile](https://images.trvl-media.com/lodging/1000000/30000/21200/21152/757dbd3e_y.jpg) ### DoubleTree by Hilton Chicago - Magnificent Mile 10/10 Excellent "Cleanliness, service " [](https://expedia.co.uk/Chicago-Hotels-DoubleTree-By-Hilton-Chicago-Magnificent-Mile.h21152.Hotel-Information) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg) ### Hilton Chicago/Magnificent Mile Suites 10/10 Excellent "Such great service, room was clean, and hotel staff were amazing! 10/10 recommend and will be staying here again when we come back!" [](https://expedia.co.uk/Chicago-Hotels-Hilton-ChicagoMagnificent-Mile-Suites.h18514.Hotel-Information) ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg) ### Congress Plaza Hotel 10/10 Excellent "Wonderful hotel" [](https://expedia.co.uk/Chicago-Hotels-Congress-Plaza-Hotel.h6452.Hotel-Information) ![Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical](https://images.trvl-media.com/lodging/1000000/30000/26000/25929/4e2c019f_y.jpg) ### Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical 10/10 Excellent "Bom atendimento! Ótima localização e quarto amplo e bem equipado!" [](https://expedia.co.uk/Chicago-Hotels-Sonesta-ES-Suites-Chicago-Downtown.h25929.Hotel-Information) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg) ### Hilton Chicago 10/10 Excellent "Great location and great hotel!" [](https://expedia.co.uk/Chicago-Hotels-Hilton-Chicago.h12570.Hotel-Information) ![Aloft Chicago Mag Mile](https://images.trvl-media.com/lodging/27000000/27000000/26998800/26998765/d755f57e_y.jpg) ### Aloft Chicago Mag Mile 10/10 Excellent "it was good" [](https://expedia.co.uk/Chicago-Hotels-Aloft-Chicago-Mag-Mile.h26998765.Hotel-Information) ![Hyatt Regency Chicago](https://images.trvl-media.com/lodging/1000000/10000/5000/4903/w3837h2157x3y3-c3ed4c01_y.jpg) ### Hyatt Regency Chicago 10/10 Excellent "Clean room, professional staff, and great location" [](https://expedia.co.uk/Chicago-Hotels-Hyatt-Regency-Chicago.h4903.Hotel-Information) ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg) ### Eurostars Magnificent Mile 10/10 Excellent "Staff was amazing! " [](https://expedia.co.uk/Chicago-Hotels-Eurostars-Magnificent-Mile.h1880320.Hotel-Information) ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg) ### Hotel Riu Plaza Chicago 10/10 Excellent "Nice" [](https://expedia.co.uk/Chicago-Hotels-Hotel-Riu-Plaza-Chicago.h102622712.Hotel-Information) ## Find out more about Chicago ## Chicago Cottages information | Number of reviews | 17 | | ----------------- | ----------- | | Accommodation | 29 Cottages | | Lowest Price | £158 | | Highest Price | £909 | ## Frequently asked questions ### Why book your cottage in Chicago with Expedia? ### How can I find cheap cottages in Chicago? ### What is there to do in Chicago near my cottage? ## Explore a world of travel with Expedia - More ways to book - [Book Cottages in Chicago on Expedia.com ](https://www.expedia.com/Chicago-Cottages.d178248-aaCottages.Travel-Guide-Accommodation)