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Chicago Metropolitan Area >
Holiday homes

Vacation Rentals Chicago Metropolitan Area, Vacation Rentals

Sorting by

Crestwood Gem

4819 142Nd St, Hotel in Crestwood, United States

Top Rated Luxury 2Br Condo Historic Location

2434 North 78Th Avenue, Unit 2W, Elmwood Park, Il 60707, Hotel in Elmwood Park, United States

Cottage With Pond At Hidden Creek Estates

13276 White School Road, Hotel in Roscoe, United States

Wrigley 4Br Home, Sleeps 10

3623 N Ashland Ave, Hotel in Chicago, United States

398 US$

min. price/night

Wicker Park 6Bd 4Ba, Steps From Cta, Parking Incl Home

1220 N Paulina, Hotel in Chicago, United States

Madison House

5200 Madison Street, Hotel in Skokie, United States

Grand Retreat 5Brs Game Room

2S661 Gray Ave, Hotel in Lombard, United States

Luxury King Sleep Number Historic Location

2434 North 78Th Avenue, Unit Ge, Elmwood Park , Il, 60707, Hotel in Elmwood Park, United States

Whimsical Historic Getaway Near Golf Skiing And Wisconsin Southern Lakes

40608 102Nd Place, Hotel in Powers Lake, United States

2 Brs & Space To Spread Out, Pets Ok, Coffee Bar

3827 Morton Avenue, Hotel in Brookfield, United States

Home With Garage In Dt Libertyville Near Naval Base

110 East Sunnyside Avenue, Hotel in Libertyville, United States

Willowbrook Gem

17W021 91St Street, Hotel in Willowbrook, United States

Bronzeville 42 Art & Hospitality

615 East 42Nd Street, Hotel in Chicago, United States

Chic 4-Bedroom Haven: Designer'S Dream Home

2655 West Huron Street, Hotel in Chicago, United States

1155 US$

min. price/night

2 Mi To Red Line Chicago Home Near Sherman Park

5205 S May St, Hotel in Chicago, United States

Tranquil Family Retreat - For 10

901 Maytag Road, Hotel in Lake Geneva, United States

Modern Farmhouse W King Bed Near Shopping

103 Willow Road, Hotel in Streamwood, United States

Monthly Or Seasonal Large Petite Lake 44 Lakehouse Retreat With Private Pier And Hot Tub Secluded Deep In The Woods

North Broadway Avenue, Hotel in Fox Lake, United States

Secluded Luxury Retreat: 15 Acres, Views, Hot Tub

7812 North Pillow Hill Road, Hotel in Spring Grove, United States

Chicago Chic, Cozy 1Br With Stylish Workspace

3114 W Waveland Ave, Unit 2A, Chicago, Il 60618, Usa, Hotel in Chicago, United States

Private Plainfield Retreat With Gas Grill And Patio

15310 S Corbin St, Hotel in Plainfield, United States

3Br Gym Workspace Chicago Condo

3656 North Osage Avenue Unit 2, Hotel in Chicago, United States

440 US$

min. price/night

Quiet Chicago Townhome Walk To Subway Stations

220 N Laporte Ave 1, Hotel in Chicago, United States

Brookfield Zoo Oasis - Families Welcome!

3626 Sunnyside Avenue, Hotel in Brookfield, United States

Enjoy Onsite Waterpark In This Family Friendly 1Bd Condo

7037 Grand Geneva Way, Hotel in Lake Geneva, United States

Cozy Retreat Amidst Serene Nature- A Perfect Getaway

Wagner Road 1130, Hotel in Porter, United States

Charming 3Bd Bungalow In Vibrant Andersonville Home

1619 W Bryn Mawr, Hotel in Chicago, United States

Secluded Lake Retreat - Private Beach, Pier & Fire Pit

28224 West Okelly Drive, Hotel in Ingleside, United States

Gary Vacation Rental Less Than 1 Mi To Indiana Dunes Np!

1127 N Warrick St, Hotel in Gary, United States

295 US$

min. price/night

Elevated Stay 3Br In Addison

419 Winthrop Avenue, Hotel in Addison, United States

Monthly And Seasonal Luxury Lakefront 5 Bedroom 5 Bath Estate

36856 N Hickory Ct, Ingleside, Il 60041, Usa, Hotel in Ingleside, United States

Updated Twin Lakes Cottage, Walk To Lake Mary

Twin Lakes, Wi, 53181, Hotel in Twin Lakes, United States

321 US$

min. price/night

3Br 2Bth Waterfront Vacation Rental On Riverwalk To Downtown Mchenry With Pier

3407 Venice Avenue, Hotel in McHenry, United States

Captain'S Quarters Lake Life Dream Home

Howard Court, Hotel in Fox Lake, United States

Bolingbrook King Bed 7 Min To Hwy & Mall

149 Galewood Drive, Hotel in Bolingbrook, United States

Spacious Family Getaway Lcp Collection

1700 Walnut Avenue, Hotel in Hanover Park, United States

3-Story Townhome Free Parking Private Patio Washer-Dryer

344 West Dickens Avenue, Hotel in Chicago, United States

237 US$

min. price/night

Cozy Rockford Home

3315 Alida Street, Hotel in Rockford, United States

Huge Projector And Designated Workspace, Near Wrigley

3116 W Waveland Ave, Unit 2B, Chicago, Il 60618, Usa, Hotel in Chicago, United States

992 US$

min. price/night

Beach Park Retreat Grill Firepit Pool Table

38369 N Manor Ave, Beach Park, Il 60087, Usa, Hotel in Beach Park, United States

Historic Lake Geneva Outpost Speakeasy House

W3619 Oakrest Avenue, Hotel in Lake Geneva, United States

Spacious 3-Bed West Loop Townhouse, 1 Car Garage

920 W Van Buren St, Hotel in Chicago, United States

Captains Quarters Lake Life Dream Home 2Bed 2Bath

188 Howard Ct, Fox Lake, Il 60020, Usa, Hotel in Fox Lake, United States

Golden Dunes Stay Valpo 5 Bedroom 3 King Beds, Game Area

558 Bond Ave, Hotel in Valparaiso, United States

Cozy Wicker Park Home With Movie Room

1523 North Artesian Avenue, Hotel in Chicago, United States

Rr Oasis

2136 Ash Street, Hotel in Des Plaines, United States

Mchenry Riverside Retreat Comfort

3719 West Freund Avenue, Hotel in McHenry, United States

Suburban Dream House

15018 104Th Ave, Hotel in Dyer, United States

The Main Stay - Mineola Bay Lakeview And Access - Fully Furnished Monthly & Seasonal Rental In Fox Lake

176 East Grand Avenue, Hotel in Fox Lake, United States

Luxury Willowbrook Getaway

17W021 91St St #2 Willowbrook, Hotel in Willowbrook, United States

Charming 5Bd 2Ba With Spacious Yard Near O'Hare

10308 West Lyndale Avenue, Hotel in Northlake, United States

Exceptional Willowbrook Retreat

17W007 91St Street, Hotel in Willowbrook, United States

The Sunset Getaway, Modern 3Br W Deck Minutes From I-65, Fenced Yard

12 Sunset Rd, Hotel in Merrillville, United States

Less Than 1 Mi To Dwtn Valparaiso Family Home

352 Park Ave, Hotel in Valparaiso, United States

Waterfront Fox Lake Vacation Rental With Fire Pit!

14 N Lake Ave, Hotel in Fox Lake, United States

363 US$

min. price/night

Cozy 4Br Home With 2By5 Baths

504 North Braintree Drive, Hotel in Schaumburg, United States

Harbor Clubhouse Modern Waterfront With Hot Tub And Pet Friendly

92 Grand Avenue, Hotel in Fox Lake, United States

Charming Oak Park 4Bd 3,5Ba And 2 Private Parking Home

422 S Lombard Ave, Hotel in Oak Park, United States

Oak Park Charm 15Min To Chi Loop

942 North Austin Boulevard, Hotel in Oak Park, United States

Cozy 5Bd 2Bth Home With Scandinavian Vibes

537 North Yale Avenue, Hotel in Villa Park, United States

Westchester Retreat King Bed

1143 Suffolk Avenue, Hotel in Westchester, United States

Surf Dweller 210 - Surf Buggy

554 Coral Court, Hotel in Schaumburg, United States

3 Mi To Hard Rock Casino Charming Home In Gary!

550 Tompkins St, Hotel in Gary, United States

The Blue Sapphire On Mineola Bay 3Br 3Ba Luxury Lakefront Home On Mineola Bay Stunning Views On Chain O Lakes

Grand Avenue, Hotel in Fox Lake, United States

Chic Green L Near Downtown & Il Medical District

602 South Western Avenue, Hotel in Chicago, United States

118 US$

min. price/night

Amazing Wicker Park Penthouse With Skyline Views

1549 North Milwaukee Avenue #4, Hotel in Chicago, United States

Ranch Single Level Home Near Downtown Tinley Park

7156 173Rd Place, Hotel in Tinley Park, United States

Cozy Harvard Home Just 1 Block From The Metra Up-Nw Line For Easy Trips To Chicago Or Lake Geneva

203 North Eastman Street, Hotel in Harvard, United States

Cozy 4-Bedroom Apartment In Evanston

1715 Payne Street, Hotel in Evanston, United States

1 Mi To Dtwn Elgin Dutch Colonial With Lovely Patio

56 S Edison Ave, Hotel in Elgin, United States

Cozy Chic 4Bd 2Ba Home In St Charles

1304 Dean Street, Hotel in Saint Charles, United States

Salem Vacation Home With Dock Steps To Paddock Lake

24333 72Nd St, Hotel in Twin Lakes, United States

Lake Geneva Family Gem With Fenced Dog Run!

203 Vernon St, Hotel in Lake Geneva, United States

Williams Bay Lakefront Retreat - Walk The Lakepath

31 N Walworth Ave, Hotel in Lake Geneva, United States

3 Bedroom Spacious Home In Ideal Location W Free Parking Back Yard Pets Welcome

1426 North North Park Avenue, Hotel in Chicago, United States

949 US$

min. price/night

Serene Oasis Near Rock River

4016 Eaton Drive, Hotel in Loves Park, United States

Walk To Wrigley Field! Townhouse With Pool Table

1045 W Dakin St Unit 1, Hotel in Chicago, United States

Sleeps 24+ Luxury House Near Chicago 12 King Beds

204 Rand Road, Hotel in Des Plaines, United States

Cozy Home Near O Hare Fast Internet

2812 South Scott Street, Hotel in Des Plaines, United States

Apt With Heated Garage Libertyville Near Naval Base

225 West Park Avenue Unit 2, Hotel in Libertyville, United States

Valpo Glow & Dunes Flow

258 Valparaiso Street, Hotel in Valparaiso, United States

The Blue Garden Escape

402 South 13Th Avenue, Hotel in Saint Charles, United States

Gated Family Home With Chefs Kitchen

1427 North Monticello Avenue, Hotel in Chicago, United States

238 US$

min. price/night

Private Oasis With Spacious Backyard

20348 Keeler Avenue, Hotel in Matteson, United States

Your Cozy Getaway With Sunroom & Gaming Room

1512 N Green Meadows Blvd, Hotel in Streamwood, United States

Spacious 5-Bedroom Retreat In Forest Park

418 Elgin Avenue, Hotel in Forest Park, United States

Heaven On Earth 2 Bdr Fontana Flat Walk To Lake

105 W Main St, Hotel in Lake Geneva, United States

Huemanns Haven - Spacious 3 Bedroom Close To Downtown

245 Elmwood Ave, Hotel in Lake Geneva, United States

Geneva Lake Adventures Family Retreat With Patio

537 Free Church Dr, Hotel in Lake Geneva, United States

Spacious 3Br Urban Getaway W Gym

2550 South Wabash Avenue, Hotel in Chicago, United States

New Home Neer Ohare

1315 Webster Lane, Hotel in Des Plaines, United States

Brand New 2 Bedroom With Office

5603 Jackie'S Drive, Hotel in Loves Park, United States

Magnolia Manor - Remodeled Home Near Downtown

413 Walworth Street, Hotel in Lake Geneva, United States

Spacious Retreat Near Convention Centers Home

1524 East Algonquin Road, Hotel in Des Plaines, United States

The Family Retreat

344 155Th Place, Hotel in Calumet City, United States

Spacious 2 Bedroom Home In Niles, Illinois With Office, Full Kitchen And 2 Baths

8509 North Ozanam Avenue, Hotel in Niles, United States

The Lake House On Myers Bay - 3-Bed 2-Bath Luxury Home With Private Pier Beach Firepit And Deck

Circle Drive, Hotel in Fox Lake, United States

Cute And Cozy Chicago Modern Condo

1625 W Superior St 3F, Chicago, Il 60622, Usa, Hotel in Chicago, United States

526 US$

min. price/night

Steps To Powers Lake Wisconsin Family Home

39511 Bloomfield Rd, Hotel in Burlington, United States

3Bed 1Bath Ranch Home Rental

408 West Kensington Road, Hotel in Mount Prospect, United States

Meyers Bay Sunset Lakefront Cottage In Fox Lake With Boat Pier

35672 North Sheridan Drive, Hotel in Fox Lake, United States

Month To Month And Seasonal Luxury Lakefront 5 Bed 5 5 Bath Estate Home

North Hickory Court, Hotel in Ingleside, United States

Como Collection - 2 Homes 2 Lakes 1 Rental

W4177 & W4181 West End Rd, Hotel in Lake Geneva, United States

Immaculate Brand New Penthouse Chicago

1630 West Warren Boulevard, Hotel in Chicago, United States

799 US$

min. price/night

Chicago 1Br, Stylish Stay With Workspace

3114 W Waveland Ave Unit 1A, Chicago, Il 60618, Usa, Hotel in Chicago, United States

Chicago Home With Spacious Yard 14 Mi To Dtwn

Chicago, United States

112 US$

min. price/night

Serene & Charming 5Br Des Plaines Getaway Home

2350 Eastview Drive, Hotel in Des Plaines, United States

728 US$

min. price/night

Charming Downtown Lake Geneva Getaway

544 Jefferson Avenue, Hotel in Lake Geneva, United States

Shop, Dine And Unwind Oak Park Home With Private Yard

1024 S Ridgeland Ave, Hotel in Oak Park, United States

Cute & Cozy Lakeview House On Chain O Lakes With Hot Tub Option

3 North Maple Avenue, Hotel in Fox Lake, United States

Classic Forest Park Foursquare Less Than 1 Mi To Blue Line

419 Thomas Ave, Hotel in Forest Park, United States

Charming Geneva Cottage Walk 4 Blks To Downtown

723 North Street, Hotel in Geneva, United States

405 Waldeck Dr

405 Waldeck Drive, Hotel in Twin Lakes, United States

Spacious 7-Bedroom Home In Evanston

1715 Payne Street, Hotel in Evanston, United States

Charming 3 Bed 1 Story Home Near Naval Base

1319 Westmoreland Avenue, Hotel in Waukegan, United States

Powers Lake Gem Peek-A-Boo Views And Beach Access

9111 Lake Park Dr, Hotel in Genoa City, United States

Farmhouse

2233 47Th Avenue, Hotel in Kenosha, United States

Cozy Westmont Home Walk To Metra Station!

16 S Hudson St, Hotel in Westmont, United States

162 US$

min. price/night

The Jackson Cottage On Grass Lake Waterfront 2 1 Nautical Cottage With Hot Tub Firepit & Year-Round Fun

39253 North Jackson Drive, Hotel in Fox Lake, United States

Beautifully Remodeled Flat Downtown #3N

858 North Orleans Street #3N, Hotel in Chicago, United States

239 US$

min. price/night

Dunes Haven

290 North Hamilton Street, Hotel in Gary, United States

Chicago Gem! Centrally Located - Proximity To O' Hare Airport

713 Norwood Lane, Hotel in Schaumburg, United States

Whimsical Historic Getaway Near Golf Skiing And Wisconsin Southern Lakes

40608 102Nd Place, Hotel in Genoa City, United States

My Happy Place

1030 Lake Geneva Boulevard, Hotel in Lake Geneva, United States

Cozy 3Br Cabin With Hot Tub On Nippersink Creek

306 Waverly Street, Hotel in Spring Grove, United States

Beautiful Remodeled Penthouse Unit In Old Town

1556 North La Salle Street, Hotel in Chicago, United States

139 US$

min. price/night

Luxe 4Br With Hot Tub & Game Room

1654 West Ohio Street, Hotel in Chicago, United States

967 US$

min. price/night

New 2 Bed With Office In Loves Park

5617 Jackie'S Drive, Hotel in Loves Park, United States

Your New Luxury Lakeview Condo W Pool Access

Aspen Road 81, Hotel in Lake Geneva, United States

106 US$

min. price/night

Charming & Bright Multilevel Townhome With Parking

Chicago, United States

Oak Park 5Bd 2Bth Sleeps 11 With 3 Private Parking

421 North Humphrey Avenue, Hotel in Oak Park, United States

Lake Como Clubhouse

N3392 Club House Drive, Hotel in Lake Geneva, United States

323 US$

min. price/night

Goose Island Central Downtown Prime Location With Access To Patio Chi - 1

West Augusta Boulevard 1220, Hotel in Chicago, United States

179 US$

min. price/night

In-Home Theater Modern Naperville Vacation Rental

3423 Goldfinch Dr, Hotel in Naperville, United States

Cozy Maple House Family Lake Como Retreat

Maple Road N3348, Hotel in Lake Geneva, United States

Relaxing Country-View Home Near Golf & Casino

2465 Centerville Road, Hotel in Rockford, United States

Oak Park Charm 15Min To Chi Loop

942 North Austin Boulevard, Hotel in Oak Park, United States

North Chi Retreatnavysaunatiki Bargames

747 Broadway Avenue, Hotel in North Chicago, United States

Mineola Bay Lakeview And Access Fully Furnished Monthly And Seasonal Rental In Fox Lake

176 East Grand Avenue, Hotel in Fox Lake, United States

Pet Friendly Lake Geneva Getaway For 6

927 Clover Street, Hotel in Lake Geneva, United States

Oak Park Downtown King Bed Rooftop Fitness Center Top Flr City View

100 Forest Place, Hotel in Oak Park, United States

389 US$

min. price/night

Lincoln Park Living - 3 Queen Beds - Sleeps 6

1147 West Diversey Parkway, Hotel in Chicago, United States

139 US$

min. price/night

Zen Escape-Chicago'S Urban Oasis

841 North Mozart Street, Hotel in Chicago, United States

79 US$

min. price/night

White Sox Best House

3801 South Calumet Avenue, Hotel in Chicago, United States

162 US$

min. price/night

Ravine Retreat

552 Ravine Drive, Hotel in Valparaiso, United States

Relax & Play - 4Br Home With Game Room For Family & Outdoor Area

1415 Glenwood Avenue, Hotel in Joliet, United States

Englishprairiebnb - 8 Bedrooms - 4 Bathrooms

1213 West Main Street, Hotel in Twin Lakes, United States

3Bed 2Bath Luxury Lake House On Myers Bay Private Pier Beach Firepit And Deck

525 Circle Dr, Fox Lake, Il 60020, Usa, Hotel in Fox Lake, United States

Luxury Artistic Condo Historic Location

2434 North 78Th Avenue, Unit 2E, Elmwood Park, Il 60707, Hotel in Elmwood Park, United States

Modern Comfort Loves Park - Stylish 3Br Getaway

784 Long Island Circle, Hotel in Belvidere, United States

The Wheaton Way

1625 Beecher Ave, Hotel in Wheaton, United States

Breathtaking Downtown Penthouse A - Sleeps 11

811 N Sedgwick St, Hotel in Chicago, United States

329 US$

min. price/night

Other Places to Stay in Chicago Metropolitan Area

Popular Areas in Chicago Metropolitan Area

Chicago Lake Geneva Rosemont Bourbonnais Glenview Arlington Heights Aurora Bloomingdale Burlington Chesterton Countryside Dwight Hammond Joliet Lombard Morris Oak Brook Schaumburg Schiller Park Woodstock Addison Algonquin Alsip Antioch Austin Bannockburn Barrington Bartlett Beach Park Bedford Park Belvidere Bensenville Berwyn Bolingbrook Bradley Bridgeview Bristol Broadview Brookfield Buffalo Grove Burbank Burr Ridge Calumet City Calumet Park Carol Stream Cary Cedar Lake Channahon Chicago Heights Chicago Ridge Cicero Country Club Hills Crestwood Crown Point Crystal Lake Darien Deer Park Deerfield DeKalb Des Plaines Dinwiddie Dolton Downers Grove Dunning Dyer East Chicago East Hazel Crest Elgin Elk Grove Village Elmhurst Elmwood Park Evanston Forest Park Fox Lake Fox River Grove Frankfort Franklin Park Gages Lake Gary Geneva Genoa City Glen Ellyn Glendale Heights Glenwood Grayslake Gurnee Hampshire Hanover Park Harvard Harvey Hebron Highland Park Hillside Hobart Hoffman Estates Homewood Huntley Ingleside Itasca Ives Grove Johnsburg Kankakee Kenosha Lake Bluff Lake Forest Lake in the Hills Lake Zurich Lansing Lemont Libertyville Lincolnshire Lincolnwood Lisle Lockport Loves Park Lowell Lyons Manteno Markham Matteson Maywood McHenry Melrose Park Merrillville Mettawa Minooka Mokena Monee Montgomery Morton Grove Mount Pleasant Mount Prospect Mundelein Munster Naperville Niles North Aurora North Chicago Northbrook Northlake Oak Forest Oak Lawn Oak Park Oakbrook Terrace Orland Park Oswego Palatine Phoenix Plainfield Plano Pleasant Prairie Portage Porter Powers Lake Prospect Heights Richmond River Grove Riverwoods Rochelle Rockford Rockton Rolling Meadows Romeoville Roscoe Roselle Saint Charles Salem Sandwich Schererville Shorewood Skokie South Holland Spring Grove Stickney Streamwood Sturtevant Sycamore Tinley Park Tolleston Twin Lakes Valparaiso Vernon Hills Villa Park Wadsworth Warrenville Waukegan West Dundee Westchester Westmont Wheaton Wheeling Whiting Willowbrook Wilmette Wilmington (Will County) Winthrop Harbor Wood Dale Worth Yorkville Zion

Types of Accomodations in Chicago Metropolitan Area

Apartments Hotels Holiday homes

Motels

Inns

Homestays

Bed & Breakfasts

Guest houses

Villas

Aparthotels

Resorts

Hostels

Lodges

Capsule hotels

Country house

Campsite

Chalet

Hotels near Popular Places to visit in Chicago Metropolitan Area

Chicago Rockford International

Chicago Midway International Airport

Chicago O'Hare International Airport Wrigley Field Navy Pier Chicago Grant Park Michigan Avenue Chicago United Center McCormick Place Chicago Union Station

Chicago Theater

Donald E. Stephens Convention Center

Naval Station Great Lakes

Millennium Park

Six Flags Great America

Brookfield Zoo

Rivers Casino

Allstate Arena

Loyola University Chicago

Chicago Riverwalk

CIBC Theatre

Gurnee Mills

House of Blues Chicago

Art Institute of Chicago

Willis Tower Chicago

Northwestern Memorial Hospital

Hollywood Casino Amphitheatre Tinley Park

Water Tower Place Chicago

Cloud Gate

Museum of Science and Industry

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