Destination: Search
Great Rentals is part of HomeAway.com, the world's leading vacation rentals marketplace. Search over 170,000 vacation rentals properties now! Click here to see more Chicago Vacation Rentals

Chicago Vacation Rental Accommodations - Page 1 of 3

Go to page 1 2 3 (1-50 of 103) Next Last
Sort by: Show rentals per page
SPECIAL OFFER! 3 nights for $360 September 19 - January 28

Chicago Sp Suite MIllenum Park

  • 1 BR/1 BA Condo (sleeps 2)
    $130 - $180/nt
    $800 - $1,000/wk
    $2,300 - $3,000/month
    per property, downtown, lake, jacuzzi, balcony, fitness room, air-conditioning, internet access, satellite or cable, TV

Chicago Gold Coast High-rise: 1 Block to Mich Ave Shopping. Best Location

  • 2 BR/2 BA Condo (sleeps 6)
    $99 - $299/nt
    $800 - $1,500/wk
    $2,200 - $4,500/month
    per property, downtown, terrace, fitness room, air-conditioning, internet access, satellite or cable, TV, DVD

Chicago Amazing Views of the Chicago Skyline from this Luxury Condo

  • 2 BR/2 BA Condo (sleeps 4)
    $125/nt
    $775/wk
    $2,250/month
    per property, downtown, lake, balcony, fitness room, air-conditioning, internet access, satellite or cable, TV, DVD

Chicago Great Value, Near Downtown & McCormick Place. Hot Tub, Amazing View, & Parking

  • 3 BR/1 BA, 1 half bath Apartment (sleeps 6)
    $125 - $195/nt
    $750 - $1,100/wk
    per property, town, sauna, air-conditioning, internet access, satellite or cable, TV, DVD, parking

Chicago SpSuites - Millenium Park

  • 1 BR/1 BA Apartment (sleeps 3)
    $110 - $180/nt
    $800 - $1,300/wk
    $2,500 - $3,400/month
    per apartment, air-conditioning, balcony, clothes dryer, dish washer, family, refrigerator, ice maker, iron & board

Chicago Wrigleyville/Southport Corridor Luxury Inn

  • 2 BR/1 BA Condo (sleeps 6)
    $179/nt
    per property, town, garden, pets considered, air-conditioning, internet access, satellite or cable, TV, DVD

Chicago Best Value!! Gorgeous 2BR Home in Mayfair/Lincoln Square Free Parking!

  • 2 BR/1 BA House (sleeps 8)
    $129 - $149/nt
    $899/wk
    per property, downtown, lake, garden, balcony, pets considered, air-conditioning, internet access, satellite or cable, TV

Chicago Luxurious Chicago Condo Overlooking Lake Michigan, Soldier Field & Museum Campus

  • 3 BR/3 BA Condo (sleeps 6)
    $400 - $450/nt
    per property, downtown, lake, balcony, pets considered, fitness room, air-conditioning, internet access, satellite or cable, TV

Chicago $99 per Bedroom* 2BR-Spectacular Modern Corner Unit in an Amazing Location!

  • 2 BR/2 BA Apartment (sleeps 6)
    $239/nt
    per apartment, air-conditioning, balcony, clothes dryer, dish washer, DVD, family, refrigerator, grill

Chicago $99 per Bedroom* 2BR -Awesome Loft! Walking Distance Downtown/Mag Mile

  • 2 BR/2 BA Condo (sleeps 6)
    $179/nt
    per condo, air-conditioning, clothes dryer, dish washer, DVD, family, refrigerator, historic, iron & board
Back to Top

Chicago 4 BR - Gorgeous Contemporary Sleek Home

  • 4 BR/3 BA House (sleeps 12)
    $449/nt
    per house, air-conditioning, clothes dryer, coffee grinder, cycling, deck wood, dish washer, DVD, family

Chicago Teri's Chicago Guest House * Wrigley Suite * Wrigleyville

  • 4 BR/2 BA Apartment (sleeps 8)
    $396 - $495/nt
    per property, downtown, lake, garden, air-conditioning, internet access, satellite or cable, TV, DVD, parking

Chicago Teri's Chicago Guest House *Clark Suite * Wrigleyville

  • 3 BR/2 BA Apartment (sleeps 8)
    $359 - $449/nt
    per property, downtown, lake, garden, air-conditioning, internet access, satellite or cable, TV, DVD, parking

Chicago $99 per Bedroom 4 BR - Near McCormick Place, Amenities Galore

  • 4 BR/3 BA, 1 half bath House (sleeps 10)
    $399/nt
    per house, air-conditioning, balcony, beach, blender, clothes dryer, cycling, deck wood, dish washer

Chicago Luxury Penthouse Lakeview/Roscoe Village A

  • 2 BR/2 BA Condo (sleeps 6)
    $225/nt
    per property, downtown, village, pool, jacuzzi, balcony, pets considered, air-conditioning, internet access, satellite or cable

Chicago Beautiful Brand-new Condo in trendy Andersonville

  • 3 BR/2 BA Condo (sleeps 8)
    $200/nt
    $1,100/wk
    $4,000/month
    per property, downtown, lake, jacuzzi, balcony, air-conditioning, internet access, satellite or cable, TV, DVD

Chicago Truly Stunning Skyline/River Views! All Luxury Perfect Location w/Free Parking!

  • 2 BR/2 BA Condo (sleeps 6)
    $199 - $249/nt
    $1,294/wk
    per property, downtown, river, balcony, fitness room, air-conditioning, internet access, satellite or cable, TV, DVD

Chicago SPACIOUS 2BR HOME BY LINCOLN SQUARE PERFECT LOCATION WALK TO TRAIN

  • 2 BR/1 BA House (sleeps 6)
    $129 - $149/nt
    $899/wk
    per property, beach, downtown, pool, terrace, pets considered, air-conditioning, internet access, satellite or cable, TV

Chicago Great City Views, Off Michigan Ave/Mag Mile Contemporary. 1BR/1BA Gold Coast

  • 1 BR/1 BA Condo (sleeps 3)
    $175 - $250/nt
    per property, downtown, pool, garden, terrace, balcony, fitness room, air-conditioning, internet access

Chicago Magnificent Mile , Gold Coast Luxury Brownstone Downtown!

  • 2 BR/2 BA Apartment (sleeps 6)
    $275 - $400/nt
    per property, downtown, lake, air-conditioning, internet access, satellite or cable, TV, DVD, fireplace
Back to Top

Chicago 20%til sept 7Luxury Penthouse in A++LincolnPark,Depaul ,'Suites of Old Town #3'

  • 2 BR/2 BA Condo (sleeps 6)
    $275/nt
    per property, beach, downtown, garden, air-conditioning, internet access, satellite or cable, TV, DVD, barbecue

Chicago ZEN Modern Luxury - steps from MagMile/Trump/Restaurants/Clubs

  • 1 BR/1 BA Condo (sleeps 6)
    $175 - $199/nt
    $1,300 - $1,399/wk
    per property, downtown, lake, tennis court, garden, terrace, air-conditioning, internet access, satellite or cable, TV

Chicago Beautiful Classic Brownstone Home

  • 5 BR/3 BA House (sleeps 13)
    $429 - $499/nt
    per property, air-conditioning, internet access, satellite or cable, TV, DVD

Chicago Teri's Chicago Guest House * Shoreline Suite * Wrigleyville

  • 3 BR/2 BA Apartment (sleeps 6)
    $299 - $379/nt
    per property, downtown, lake, garden, air-conditioning, internet access, satellite or cable, TV, DVD

Chicago Teri's Chicago Guest House * Lakeview Suite * Wrigleyville

  • 3 BR/2 BA Condo (sleeps 6)
    $299 - $379/nt
    per property, downtown, lake, garden, terrace, air-conditioning, internet access, TV, DVD

Chicago Luxury Resort in the Heart of Downtown Chicago

  • 2 BR/2 BA Condo (sleeps 5)
    $320 - $360/nt
    $1,850/wk
    $5,000/month
    per property, downtown, lake, tennis court, garden, terrace, balcony, pets considered, fitness room, air-conditioning

Chicago 600 feet from Wrigley Home Plate.... but an elegant world away!

  • 2 BR/1 BA Condo (sleeps 8)
    $425/nt
    per property, downtown, town, garden, balcony, pets considered, air-conditioning, internet access, satellite or cable, TV

Chicago The Penthouse at Grand Plaza

  • 3 BR/2 BA Condo (sleeps 8)
    $525 - $625/nt
    per property, downtown, lake, sauna, balcony, fitness room, air-conditioning, internet access, satellite or cable, TV

Chicago Teri's Chicago Guest House * Belmont Suite* Wrigleyville

  • 2 BR/1 BA Apartment (sleeps 4)
    $199 - $249/nt
    per property, downtown, lake

Chicago 6 Star Hotel like 4-Story French Style House Next to the McCormick Place

  • 4 BR/2 BA, 1 half bath House (sleeps 12)
    $499 - $549/nt
    per property, downtown, river, garden, balcony, air-conditioning, internet access, DVD, parking
Back to Top

Chicago Classic 3 Bedroom Victorian Greystone in Chicago's Wrigleyville!

  • 3 BR/1 BA Apartment (sleeps 5)
    $2,205/wk
    per property, downtown, lake, balcony, air-conditioning, internet access, TV, DVD

Chicago Gold Coast Brownstone---Steps from Mag Mile/Michigan Ave Shops

  • 2 BR/1 BA Apartment (sleeps 6)
    $300/nt
    $1,800/wk
    $4,500/month
    per property, downtown, lake, balcony, pets considered, fitness room, air-conditioning, internet access, satellite or cable, TV

Chicago Great holiday hotel alternative while visiting family in the area!

  • 2 BR/1 BA House (sleeps 6)
    $115 - $130/nt
    $650/wk
    $1,800/month
    per property, air-conditioning, internet access, satellite or cable, TV, DVD

Chicago Luxurious SF House in Heart of Wrigleyville, Fall Special

  • 4 BR/3 BA House (sleeps 10) downtown, lake, jacuzzi, garden, terrace, air-conditioning, internet access, satellite or cable, TV

Chicago Modern 3 Bedroom Condo in Chicago West Lakeview

  • 3 BR/2 BA Condo (sleeps 9)
    $375 - $400/nt
    $2,600/wk
    per property, downtown, lake, jacuzzi, terrace, balcony, pets considered, air-conditioning, internet access, satellite or cable

Chicago Large Luxury Home near Downtown Chicago

  • 5 BR/4 BA, 1 half bath House (sleeps 15) downtown, river, daily maid service, jacuzzi, sauna, garden, terrace, balcony, air-conditioning

Chicago March/April Special! Amazing 2 BR Towering Over Chicago

  • 2 BR/1 BA Condo (sleeps 4)
    $225/nt
    $1,400/wk
    $6,500/month
    per property, downtown, pool, air-conditioning, internet access, satellite or cable, DVD

Chicago Downtown Waterfront Property with City Views

  • 3 BR/3 BA Townhome (sleeps 10)
    $550 - $600/nt
    $3,600/wk
    $8,000/month
    per property, downtown, river, garden, balcony, air-conditioning, internet access, satellite or cable, TV, DVD

Chicago Massive! 1800 Sq. Ft Corner unit Overlooking Lake Michigan, City and Navy Pier!

  • 3 BR/2 BA, 1 half bath Apartment (sleeps 8)
    $399 - $425/nt
    $2,495/wk
    $9,500/month
    per property, downtown, lake, sauna, fitness room, air-conditioning, internet access, satellite or cable, TV, DVD

Chicago $129 per Bedroom* 2BR- Gorgeous Condo w/ Incredible view Downtown/Michigan Ave

  • 2 BR/2 BA Condo (sleeps 6) adventure, air-conditioning, beach, beach chairs, clothes dryer, cycling, deck wood, dish washer
Back to Top

Chicago $129 per Bedroom* 2BR -Beautiful Dwntown Condo with a Splendid View Dwntwn/Michigan Ave/Grand Park

  • 2 BR/2 BA Condo (sleeps 6) air-conditioning, beach, clothes dryer, cycling, deck wood, dish washer, DVD, family

Chicago $129 per Beroom 1BR - Loop Timber Loft near Downtown/Michigan Ave/Grant Park

  • 1 BR/1 BA Condo (sleeps 4) air-conditioning, clothes dryer, cycling, dish washer, family, refrigerator, iron & board, luxury

Chicago $99 per Bedroom* 6BR-Magnificent Luxury Single Family Home Wrigleyville

  • 6 BR/5 BA Apartment (sleeps 12) adventure, air-conditioning, balcony, beach, beach chairs, blender, books, child's highchair

Chicago $129 per Bedroom* 4BR-Luxurious Home with Breathtaking Panoramic View of Skyline

  • 4 BR/3 BA House (sleeps 10) air-conditioning, balcony, beach, chauffeur, clothes dryer, cycling, deck wood, dish washer

Chicago $129 per Bedroom* 2BR- Amazing PentHouse Amazing Views of Dwntwn/Michigan Ave

  • 2 BR/2 BA Condo (sleeps 6) adventure, air-conditioning, balcony, barbecue, beach, beach chairs, chauffeur, clothes dryer

Chicago $99 per Bedroom* 7 BR - Breathtaking Luxury Home Minutes from Wrigleyville!

  • 7 BR/5 BA House (sleeps 6) adventure, air-conditioning, balcony, barbecue, beach, chauffeur, clothes dryer, cycling

Chicago $99 per Bedroom 6BR-Spacious Luxurious Home in Beautiful Lincoln Park!

  • 6 BR/4 BA, 1 half bath House (sleeps 14) air-conditioning, balcony, beach, clothes dryer, cycling, deck wood, dish washer, DVD

Chicago $99 per Bedroom* 4 BR - Brand New, Luxurious 3 Level Brick Home

  • 4 BR/3 BA, 1 half bath House (sleeps 12) air-conditioning, balcony, beach, clothes dryer, cycling, deck wood, dish washer, DVD

Chicago $89 per Bedroom* 9 BR -Breathtaking Graystone Just Minutes Wrigley Field

  • 9 BR/6 BA House (sleeps 21) adventure, air-conditioning, balcony, clothes dryer, cycling, dish washer, DVD, family

Chicago $129 per Bedroom* 4BR - Beautiful New Home near Wrigleyville!

  • 4 BR/6 BA House (sleeps 10) adventure, air-conditioning, balcony, blender, clothes dryer, cycling, deck wood, dish washer
Back to Top
Go to page 1 2 3 (1-50 of 103) Next Last

© 1996-Present HomeAway.com, Inc. All rights reserved.

Use of this Web site constitutes acceptance of the GreatRentals.com Terms and Conditions and Privacy Policy.