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Chicago Vacation Rentals

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Windy City Whispers - Chicago, IL Vacation Rental

Windy City Whispers

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - - 215 188 203 208 294 437 422 - - - - - 437 469
Chicago Wind - Chicago, IL Vacation Rental

Chicago Wind

Chicago, IL
1 Bed 1 Bath Sleeps 4
- - - - - 135 146 207 306 296 - - - - 207 323 312
Fashionable on the 42nd Floor - Chicago, IL Vacation Rental
- - - 183 - - - - - - 219 - - - - - -
State Street Retreat - Chicago, IL Vacation Rental

State Street Retreat

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - - - 179 203 208 294 437 445 257 - - - 295 460 469
Chicago Chic - Chicago, IL Vacation Rental

Chicago Chic

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - 361 - - - 251 311 460 469
Grand Plaza Perfection - Chicago, IL Vacation Rental

Grand Plaza Perfection

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - - 215 188 203 208 294 437 445 257 - - - 295 460 445
Skyline Sparkler - Chicago, IL Vacation Rental

Skyline Sparkler

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - - - - 192 208 294 437 445 257 - - - 295 460 469
Grand Avenue Getaway - Chicago, IL Vacation Rental

Grand Avenue Getaway

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - - - - - - 280 437 445 257 - - - - - -
The Skyline - Chicago, IL Vacation Rental

The Skyline

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - - - - - - 280 373 - - - - - - - -
Magnificent Mile Majesty - Chicago, IL Vacation Rental

Magnificent Mile Majesty

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - - 193 161 - - - 415 422 - - - - 295 393 -
Top of the Lake - Chicago, IL Vacation Rental

Top of the Lake

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - - 183 - - 198 294 437 445 257 - - - - - -
Downtown Dreamer - Chicago, IL Vacation Rental

Downtown Dreamer

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - - - - - - 280 437 422 - - - - 252 - -
Windy City Wonder - Chicago, IL Vacation Rental

Windy City Wonder

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - 357 215 - - - 239 - - - - - - 295 460 469
Grand Vista - Chicago, IL Vacation Rental

Grand Vista

Chicago, IL
1 Bed 1 Bath Sleeps 4
- 240 - - 113 128 131 177 - - 154 - - - 207 323 329
Urban Grandeur - Chicago, IL Vacation Rental

Urban Grandeur

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Grand Plaza Getaway  - Chicago, IL Vacation Rental

Grand Plaza Getaway

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - - 183 - - - 280 437 445 257 - - - 295 460 469
Windy City Luxury - Chicago, IL Vacation Rental

Windy City Luxury

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - - 215 188 203 208 294 437 445 270 251 - - 295 460 469
Second City Comfort - Chicago, IL Vacation Rental

Second City Comfort

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - - - - - 198 294 437 445 270 251 - - - - -
Down on State Street - Chicago, IL Vacation Rental

Down on State Street

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - - 215 188 203 208 294 437 445 270 251 - - - - -
Second City Suite - Chicago, IL Vacation Rental

Second City Suite

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - - - - 164 - - - - - - - - 295 460 469
River North Retreat - Chicago, IL Vacation Rental

River North Retreat

Chicago, IL
2 Bed 2 Bath Sleeps 6
- - - 183 - - - - - - - - - - - - -
Chi-Town Splendor - Chicago, IL Vacation Rental

Chi-Town Splendor

Chicago, IL
1 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - 307 329

About Chicago

Like beacons rising from the plains of the American Midwest, the skyscrapers of Chicago tower over the nation's third-largest city. Home to 26 miles of lakeshore and more world-class restaurants than there is time to count, the Windy City draws tens of millions of visitors to its streets each year. Whether you're a business traveler, a food lover, or a hopeless baseball fanatic, you'll find a home away from home in our Chicago vacation rentals.

Neighborhoods of Chicago, IL

With boundaries that stretch across 237 square miles, Chicago is best approached as a collection of neighborhoods - 77 to be exact, each with its own distinct character.

Within downtown Chicago, you can wander through a maze of skyscrapers in The Loop (named for the "L" tracks that encircle it) and find endless opportunities to shop on Michigan Avenue's Magnificent Mile. Head northward to join the throngs of Cubs fans in Wrigleyville, enjoy Lake Michigan's sandy shores in Lakeview, spend a day boutique shopping in Wicker Park, and graze in the green spaces of Lincoln Park. If make your way south, you'll find the prestigious University of Chicago in Hyde Park and the wide public beaches that line the South Shore.

Things to Do in Chicago, IL

In a city with more than 200 theaters and 15 miles of swimming beaches, guests at our Chicago vacation homes will find no shortage of year-round activities.

Take a ride on the L to survey the scene around The Loop, and stand at the base of the 110-story Willis Tower to gaze at the tallest building in the Western Hemisphere. Hop on board an architectural boat tour of the Chicago River, spend a rainy day touring the Art Institute of Chicago or the Museum of Science and Industry, and catch at least one home game in the stands at Wrigley Field.

The famed Lincoln Park Zoo is the oldest public zoo in the United States, and is one of only three to offer free admission. You can also rent bikes to ride on more than 19 miles of lakefront bike paths, pack a picnic for lunch alongside "The Bean" in Millennium Park, and catch an evening performance at The Second City, the Chicago Theatre, Jazz Showcase, or Green Mill.

Whether it's summer or winter, for business or pleasure, our Chicago vacation rentals will show you the best of the Windy City!

Photo Credit: Pedro Szekely via Flickr

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