Title: Chicago Holiday Homes from £146: Search Holiday Homes in Chicago | 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 holiday homes ![Interior](https://images.trvl-media.com/lodging/123000000/122590000/122582000/122581902/w1432h1080x94y0-5a95ad03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122590000/122582000/122581902/w1432h1080x94y0-7ee1aa63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, travel cot, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122590000/122582000/122581902/w1433h1080x93y0-253226e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/123000000/122590000/122582000/122581902/w1432h1080x94y0-2c40f522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Near Lake and Museum • Modern • Game Area [](https://www.expedia.co.uk/Chicago-Hotels-Walk-To-The-Lake-Grill.h122581902.Hotel-Information) South Shore £331 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Walk-To-The-Lake-Grill.h122581902.Hotel-Information) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120550000/120544700/120544690/w903h683x60y0-f205b528.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/121000000/120550000/120544700/120544690/w905h683x60y0-d3c62524.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/121000000/120550000/120544700/120544690/w904h683x60y0-92c8079f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120550000/120544700/120544690/w908h683x58y0-0a2075c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Back Unit Patio, Balcony, Yard, Smart TVs, W/D [](https://www.expedia.co.uk/Chicago-Hotels-Back-Unit-Patio.h120544690.Hotel-Information) Westmont £201 includes taxes & fees 8 Feb - 9 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Back-Unit-Patio.h120544690.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/w953h720x163y0-0c76a558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/cf096b64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/64fce148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/50000000/49100000/49092500/49092456/d1a40a0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A quiet stay while you are away [](https://www.expedia.co.uk/Chicago-Hotels-A-Quiet-Stay-While-You-Are-Away.h49092456.Hotel-Information) Oak Park 9.8/10 Exceptional (34 reviews) "great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) matt R. £162 includes taxes & fees 3 Mar - 4 Mar [](https://www.expedia.co.uk/Chicago-Hotels-A-Quiet-Stay-While-You-Are-Away.h49092456.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/d658c7db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/a541fdcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/d30bfd55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/124000000/123480000/123479400/123479305/d0b74272.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard [](https://www.expedia.co.uk/Chicago-Hotels-Charming-2BR-Hideaway-FLW-District-TheaterGamesLaundryOfficePrivate-Backyard.h123479305.Hotel-Information) Oak Park 10/10 Exceptional (1 review) "Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Willow M. £209 includes taxes & fees 10 Feb - 11 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Charming-2BR-Hideaway-FLW-District-TheaterGamesLaundryOfficePrivate-Backyard.h123479305.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/122000000/121610000/121606000/121605980/w4000h2707x0y0-0d2f41b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/122000000/121610000/121606000/121605980/fe27c4de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/122000000/121610000/121606000/121605980/32f3ec4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/122000000/121610000/121606000/121605980/3cbfee83_edited_fcc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home -2 bedroom, 4k projector [](https://www.expedia.co.uk/Chicago-Hotels-Value-Stay-Unfurnished-Home-Bring-Own-Sleeping-Beds-Or-Ask-For-Airbed-Wifi.h121605980.Hotel-Information) Waukegan 9.0/10 Wonderful (4 reviews) "Very nice stay, plenty of room with a garage and very quiet. Great location to the naval base recruit graduation. Owner was in constant contact and very helpful!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tim and kelsey J. £202 includes taxes & fees 14 Feb - 15 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Value-Stay-Unfurnished-Home-Bring-Own-Sleeping-Beds-Or-Ask-For-Airbed-Wifi.h121605980.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/33000000/32070000/32068000/32067984/7966b3f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/33000000/32070000/32068000/32067984/5445a025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/33000000/32070000/32068000/32067984/3e0125af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32070000/32068000/32067984/2718fcef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quaint Bungalow, near Great Lakes Naval Base [](https://www.expedia.co.uk/Chicago-Hotels-Quaint-Bungalow.h32067984.Hotel-Information) Mundelein 9.8/10 Exceptional (69 reviews) "Super cozy!! The neighborhood is so so so lovely! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea M. £247 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/Chicago-Hotels-Quaint-Bungalow.h32067984.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811972/acc33991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811972/337409c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811972/fba7b9ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![8 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/123000000/122820000/122812000/122811972/feda95b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleeps 18 • 8BR • Game Room • Gym • Theater [](https://www.expedia.co.uk/Chicago-Hotels-Sleeps-18-8BR-Game-Room-Gym-Theater.h122811972.Hotel-Information) Portage Park £610 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Sleeps-18-8BR-Game-Room-Gym-Theater.h122811972.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/b80be72b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w906h683x59y0-ad8ac03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w903h683x60y0-a4b1b07a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, ping pong, books](https://images.trvl-media.com/lodging/96000000/95140000/95134600/95134539/w905h683x59y0-8cb3eda8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago! [](https://www.expedia.co.uk/Chicago-Hotels-PROMO-10WEEKLY-12-MONTHLY-DISCJacuzzi.h95134539.Hotel-Information) Westchester 9.8/10 Exceptional (20 reviews) "Great place Great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Josh W. £300 includes taxes & fees 12 Feb - 13 Feb [](https://www.expedia.co.uk/Chicago-Hotels-PROMO-10WEEKLY-12-MONTHLY-DISCJacuzzi.h95134539.Hotel-Information) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/124000000/123430000/123422200/123422190/de44375b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/124000000/123430000/123422200/123422190/79bec13a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, travel cot, free WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123430000/123422200/123422190/418b6727.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123430000/123422200/123422190/f08436cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 20 min to O'Hare Airport, 20 min to Schamburg [](https://www.expedia.co.uk/Chicago-Hotels-20-Min-To-OHare-Airport.h123422190.Hotel-Information) Addison 10/10 Exceptional (2 reviews) "Definitely recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer H. £316 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Chicago-Hotels-20-Min-To-OHare-Airport.h123422190.Hotel-Information) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/103000000/102080000/102077900/102077861/615eda4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/103000000/102080000/102077900/102077861/d5f858e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102080000/102077900/102077861/1292b816.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/103000000/102080000/102077900/102077861/ef0ce419.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Heaven Retreat, 6 Bedroom, Sleep 16 [](https://www.expedia.co.uk/Chicago-Hotels-Family-Heaven-Retreat.h102077861.Hotel-Information) Carol Stream 9.6/10 Exceptional (7 reviews) "Host was very receptive to any damages that needed fixing, beds were comfy and clean, and kitchen is wonderful! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniella S. £465 includes taxes & fees 10 Feb - 11 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Family-Heaven-Retreat.h102077861.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/33378924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/aa9396b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/3f6e4959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/106000000/105140000/105136600/105136524/c4f6c687.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vintage Urban Retreat [](https://www.expedia.co.uk/Chicago-Hotels-Vintage-Urban-Retreat.h105136524.Hotel-Information) Oak Park 10/10 Exceptional (14 reviews) "This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas P. £337 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Vintage-Urban-Retreat.h105136524.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122660000/122655500/122655441/443df914.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel cot, WiFi](https://images.trvl-media.com/lodging/123000000/122660000/122655500/122655441/4de72921.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122660000/122655500/122655441/230d1f90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, video games](https://images.trvl-media.com/lodging/123000000/122660000/122655500/122655441/d8cc6f64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Stylish Comfort Near Casino and Hwy [](https://www.expedia.co.uk/Chicago-Hotels-Modern-Stylish-Comfort-Near-Casino-And-Hwy.h122655441.Hotel-Information) Homewood £303 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Modern-Stylish-Comfort-Near-Casino-And-Hwy.h122655441.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90010000/90008300/90008221/6ff9d9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/91000000/90010000/90008300/90008221/dfe845a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90010000/90008300/90008221/b41a793a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90010000/90008300/90008221/35aa2d12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury House minutes away from O'Hare and Downtown Chicago [](https://www.expedia.co.uk/Chicago-Hotels-Luxury-House-Minutes-Away-From-OHare-And-Downtown-Chicago.h90008221.Hotel-Information) Bensenville 10/10 Exceptional (1 review) "Easily the nicest place I have ever stayed at. Wonderful neighborhood, clean house, and great amenities. I’ll stay there again anyday. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacob F. £383 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Luxury-House-Minutes-Away-From-OHare-And-Downtown-Chicago.h90008221.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/793bb6f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/0900c857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/e028cf83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, travel cot, free WiFi](https://images.trvl-media.com/lodging/91000000/90620000/90612900/90612832/cb5bf3e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oak Park Victorian by FLW Studio [](https://www.expedia.co.uk/Chicago-Hotels-Modern-Victorian-Vibes-Character-Charm.h90612832.Hotel-Information) Oak Park 10/10 Exceptional (29 reviews) "Great location and walkable to restaurants. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura B. £349 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Modern-Victorian-Vibes-Character-Charm.h90612832.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/109000000/108520000/108512800/108512727/9fa07f1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108520000/108512800/108512727/a8dc63ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/109000000/108520000/108512800/108512727/2cadb1cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108520000/108512800/108512727/bfc99d13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Deck & Balcony, Game Area, Garage [](https://www.expedia.co.uk/Chicago-Hotels-Spacious-Deck-Balcony.h108512727.Hotel-Information) Glen Ellyn 9.6/10 Exceptional (20 reviews) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason T. £347 includes taxes & fees 8 Feb - 9 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Spacious-Deck-Balcony.h108512727.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/591973f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/ca60baaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/079e5c97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/49000000/48960000/48959700/48959659/76fecaef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Master qtr close to nature & easy urban facilities [](https://www.expedia.co.uk/Chicago-Hotels-Master-Qtr-Close-To-Nature-Easy-Urban-Facilities.h48959659.Hotel-Information) Riverwoods 9.8/10 Exceptional (77 reviews) "Nice , private and peaceful definitely will be back " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) BRANDEN J. £146 includes taxes & fees 17 Feb - 18 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Master-Qtr-Close-To-Nature-Easy-Urban-Facilities.h48959659.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/7b6dc406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel cot, free WiFi](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/5569ce20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/932d3e6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71680000/71677300/71677273/26045e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### \*The Comfy King Ranch\*King Bed Suite\*Fast Wi-Fi [](https://www.expedia.co.uk/Chicago-Hotels-The-Comfy-King-Ranch-King-BedFast-WiFiFree-Pkg.h71677273.Hotel-Information) Worth 9.4/10 Exceptional (56 reviews) "Very clean and comfortable! Great place for our short stay! So much space it was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David L. £241 includes taxes & fees 9 Feb - 10 Feb [](https://www.expedia.co.uk/Chicago-Hotels-The-Comfy-King-Ranch-King-BedFast-WiFiFree-Pkg.h71677273.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119940000/119934600/119934530/eb62ac02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119940000/119934600/119934530/d7abc984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119940000/119934600/119934530/82961acb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119940000/119934600/119934530/c2706618.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two Kings Chicago A unique royal environment, kingly comfort! [](https://www.expedia.co.uk/Chicago-Hotels-Your-Private-Sanctuary.h119934530.Hotel-Information) Villa Park 10/10 Exceptional (1 review) "Art & Milda were fantastic hosts! Very responsive to all inquiries and requests. The home was beautiful. Very comfy beds and recliners! So many perks you never knew you wanted. Will definitely stay again. Thank you Art & Milda!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa V. £354 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Your-Private-Sanctuary.h119934530.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/123000000/122070000/122068900/122068878/b289aa5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/123000000/122070000/122068900/122068878/bb6345e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/123000000/122070000/122068900/122068878/0e77b64b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/123000000/122070000/122068900/122068878/f7cf3b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly remodeled Near Lake 4BR Hot Tub Navy Family home [](https://www.expedia.co.uk/Chicago-Hotels-Newly-Remodeled-Near-Lake-4BR-W-Hot-Tub-Games.h122068878.Hotel-Information) Gages Lake 10/10 Exceptional (2 reviews) "Nice location for our family attending our daughter's graduation from Navy Basic at Great Lakes. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Judson S. £394 includes taxes & fees 15 Feb - 16 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Newly-Remodeled-Near-Lake-4BR-W-Hot-Tub-Games.h122068878.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/85000000/84320000/84314800/84314776/89651141.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/85000000/84320000/84314800/84314776/w1018h683x3y0-7ed1e010.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel cot](https://images.trvl-media.com/lodging/85000000/84320000/84314800/84314776/w1019h683x3y0-935e50e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, offices](https://images.trvl-media.com/lodging/85000000/84320000/84314800/84314776/e14752ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard [](https://www.expedia.co.uk/Chicago-Hotels-Comfy-Home-W-Access-To-Major-RoadsHwys.h84314776.Hotel-Information) Lombard 9.6/10 Exceptional (17 reviews) "I had a great stay over the weekend with my family it was very relaxing and peaceful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tennika W. £208 includes taxes & fees 8 Feb - 9 Feb [](https://www.expedia.co.uk/Chicago-Hotels-Comfy-Home-W-Access-To-Major-RoadsHwys.h84314776.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) 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) 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) 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) 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) 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-Private-Holiday-Homes.d178248-aaPrivateHolidayHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChicago-Private-Holiday-Homes.d178248-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ## Top Chicago Hotel Reviews ![Courtyard by Marriott Chicago Magnificent Mile](https://images.trvl-media.com/lodging/1000000/990000/982600/982517/529d8be8_y.jpg) ### Courtyard by Marriott Chicago Magnificent Mile 10/10 Excellent "Great room, very quiet and staff was friendly and accomodating." [](https://expedia.co.uk/Chicago-Hotels-Courtyard-By-Marriott-Chicago-Magnificent-Mile.h982517.Hotel-Information) ![The Royal Sonesta Chicago Downtown](https://images.trvl-media.com/lodging/1000000/20000/17600/17543/696a55e6_y.jpg) ### The Royal Sonesta Chicago Downtown 10/10 Excellent "Great overall hotel and the best River view." [](https://expedia.co.uk/Chicago-Hotels-Royal-Sonesta-Chicago-Downtown.h17543.Hotel-Information) ![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) ## Find out more about Chicago ## Chicago Holiday Homes information | Number of reviews | 345 | | ----------------- | ----------------- | | Accommodation | 822 Holiday Homes | | Lowest Price | £146 | | Highest Price | £610 | ## Explore a world of travel with Expedia - Accommodation - Packages - Cars - Holiday Homes - Other - More ways to book - [Hotels near 311 S Wacker Dr ](https://www.expedia.co.uk/311-S-Wacker-Dr-Hotels.0-l6069157-0.Travel-Guide-Filter-Hotels) - 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