Vacation Rentals in Chicago, Illinois
Chicago, Illinois Vacation Rentals and Tourism
It’s impossible to return home from a Chicago vacation without feeling a lot more enlightened and cultured. (And without more belongings - Chicago's one of our favorite shopping destinations.) The world-famous city in Illinois has open arms for everybody, no matter their age, background, or lifestyle. So no matter who you are or where you're from, Chicago vacation rentals are right up your alley.
The exquisite jazz and blues clubs will delight music lovers. Wrigley Field will thrill those who enjoy America’s favorite pastime, baseball. Kids (and their parents too) will lose track of time at the attraction-filled Navy Pier and Lincoln Park Zoo. Museum hoppers won’t ever run out of things to do, which will likely include a tour of the Art Institute of Chicago. And everybody will be intrigued by the many historical and architectural landmarks, like the famous Sears Tower. Don’t forget to spend at least one day in Millennium Park, which offers up adventure year-round (in the winter, you can ice skate). Also, Michigan Lake is always fun when it’s sunny out.
If a Chicago vacation house doesn’t sound appealing to you by now, then perhaps you’re concerned about how affordable your getaway will be! Fortunately, thanks to the many Chicago vacation rentals found here, you can definitely find cheap accommodations. Whether it’s a Chicago weekly condo rental or one-night accommodation you’re interested in, you can find it right here. And in fact, although dining out in Chicago is an unforgettable experience in itself, you still have the option to save money and dine in because your Chicago luxury condo rental will surely have a kitchen. You certainly can’t say the same for a hotel.
Chicago vacation apartments are extremely popular as they allow tourists to really enjoy the vibrant local culture of the city. Don’t hide away in a resort hotel; instead stay in one of the cozy Chicago condo rentals found here! There’s a reason people keep coming back to this rich and exciting city, so why don’t you experience it for yourself by booking one of the Chicago vacation apartments or houses listed here?
Sights and tours to see
Wrigley Field
Navy Pier
Lincoln Park Zoo
Art Institute of Chicago
Sears Tower
Millennium Park
Michigan Lake
Chicago Vacation Rental Deals
Chicago is the home of activity, with hundreds of entertainment options from live music to original cuisine there not shortage of things to do. Take a break from life and visit Chicago. Worried about the expenses? Don’t be, with our discounted Chicago vacation rentals, you can afford to stay in luxury Chicago accommodations without spending a lot. Don’t let your budget slow you down—with cheap Chicago vacation rentals, you’ll be able to enjoy everything the windy city has to offer even if you go for last-minute rental deals on Chicago rentals. We won’t leave your wallet disappointed with our cheap rates.
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Check out more areas which feature homes, villas, cabins, cottages, or condos.
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50% off = $110 per night
- bedrooms 1
- sleeps 2
- community Streeterville
- baths 1
- rental type Apartment
-
rates (USD)
$145
-
$220
/nt
$1,000 - $1,400 /wk
$2,600 - $3,500 /mth
-
50% off = $100 per night
- bedrooms 1
- sleeps 3
- community Lincoln Park
- baths 1
- rental type Apartment
-
rates (USD)
$150
-
$200
/nt
$1,200 - $1,400 /wk
$2,800 - $3,500 /mth
-
$75 off = $250 per night
- bedrooms 3
- sleeps 40
- community
- baths 2½
- rental type Condo
-
rates (USD)
$325
-
$325
/nt
-
$65 off = $100 per night
- bedrooms 1
- sleeps 1
- community
- baths 1
- rental type House
-
rates (USD)
$165
-
$165
/nt
-
$45 off = $115 per night
- bedrooms 1
- sleeps 4
- community
- baths 1
- rental type Condo
-
rates (USD)
$160
-
$160
/nt
-
$50 off = $200 per night
- bedrooms 2
- sleeps 30
- community
- baths 2
- rental type Condo
-
rates (USD)
$250
-
$300
/nt
-
$50 off = $275 per night
- bedrooms 16
- sleeps 30
- community
- baths 14
- rental type Condo
-
rates (USD)
$325
-
$325
/nt
-
$400 off = $1,100 per week
- bedrooms 2
- sleeps 4
- community
- baths 2
- rental type Apartment
-
rates (USD)
$250
-
$320
/nt
$1,200 - $2,100 /wk
$4,000 - $6,000 /mth
-
50% off = $300 per week
- bedrooms 1
- sleeps 2
- community
- baths 1
- rental type Apartment
-
rates (USD)
$450
-
$600
/wk
-
Fall Shopping Spree Sale
($250)
- bedrooms 2
- sleeps 6
- community
- baths 1
- rental type Apartment
-
rates (USD)
$119
-
$119
/nt
$735 - $735 /wk
-
Fall Shopping Spree Sale
($250)
- bedrooms 2
- sleeps 7
- community
- baths 1
- rental type Apartment
-
rates (USD)
$119
-
$119
/nt
$735 - $735 /wk
-
$25 off = $100 per night
- bedrooms 1
- sleeps 4
- community
- baths 1
- rental type Condo
-
rates (USD)
$125
-
$125
/nt
$750 - $750 /wk
-
10% off = $198 per night
- bedrooms 2
- sleeps 5
- community Downtown Chicago
- baths 1
- rental type Condo
-
rates (USD)
$200
-
$220
/nt
$1,400 - $1,600 /wk
-
10% off = $135 per night
-
Wireless Internet and Laundry
($20)
- bedrooms 2
- sleeps 5
- community Lincoln Park
- baths 1
- rental type Duplex
-
rates (USD)
$150
-
$200
/nt
$900 - $1,400 /wk
$2,600 - $3,200 /mth
- bedrooms 0
- sleeps 1
- community the New East Side
- baths ½
- rental type Studio
-
rates (USD)
$1
-
$2
/nt
$3 - $4 /wk
- bedrooms 0
- sleeps 4
- community South Loop
- baths 1
- rental type Studio
-
rates (USD)
$950
-
$1,100
/wk
- bedrooms 1
- sleeps 3
- community 30 East Huron
- baths 1
- rental type Condo
-
rates (USD)
$149
-
$225
/nt
$1,200 - $1,600 /wk
- bedrooms 1
- sleeps 7
- community River City
- baths 1
- rental type Condo
-
rates (USD)
$100
-
$150
/nt
$750 - $1,000 /wk
$1,750 - $2,700 /mth
- bedrooms 1
- sleeps 2
- community 1400 N Lake Shore Dr
- baths 1
- rental type Condo
- rates (USD) $1,400 - $2,750 /mth
- bedrooms 1
- sleeps 4
- community Chicago
- baths 1
- rental type Condo
-
rates (USD)
$1
-
$1
/nt
- bedrooms 1
- sleeps 2
- community Andersonville/ Edgew
- baths 1
- rental type Studio
-
rates (USD)
$99
-
$149
/nt
$693 - $1,043 /wk
$2,772 - $4,172 /mth
- bedrooms 2
- sleeps 4
- community
- baths 1
- rental type Condo
-
rates (USD)
$200
-
$220
/nt
$1,400 - $1,540 /wk
- bedrooms 2
- sleeps 6
- community
- baths 1
- rental type House
-
rates (USD)
$2,000
-
$6,000
/wk
- bedrooms 2
- sleeps 4
- community Andersonville/ Edgew
- baths 1
- rental type Apartment
-
rates (USD)
$99
-
$149
/nt
$693 - $1,043 /wk
$2,772 - $4,172 /mth
- bedrooms 2
- sleeps 8
- community
- baths 1
- rental type Condo
-
rates (USD)
$245
-
$425
/nt
$1,200 - $2,000 /wk
$3,600 - $4,500 /mth
- bedrooms 2
- sleeps 6
- community Michigan Ave
- baths 2
- rental type Condo
-
rates (USD)
$195
-
$450
/nt
$1,000 - $2,000 /wk
- bedrooms 2
- sleeps 4
- community Condominium
- baths 2
- rental type Condo
-
rates (USD)
$1,700
-
$1,700
/wk
- bedrooms 2
- sleeps 4
- community Lakeview
- baths 2
- rental type Apartment
-
rates (USD)
$98
-
$150
/nt
$680 - $980 /wk
$2,050 - $2,650 /mth
- bedrooms 2
- sleeps 7
- community River North
- baths 2
- rental type Condo
-
rates (USD)
$1,800
-
$2,500
/wk
- bedrooms 2
- sleeps 4
- community
- baths 2
- rental type Condo
-
rates (USD)
$275
-
$400
/nt
$1,500 - $2,000 /wk
$3,500 - $4,000 /mth
- bedrooms 2
- sleeps 6
- community Chicago
- baths 2
- rental type Condo
-
rates (USD)
$1
-
$1
/nt
- bedrooms 2
- sleeps 6
- community Chicago
- baths 2
- rental type Condo
-
rates (USD)
$1
-
$1
/nt
- bedrooms 2
- sleeps 6
- community Chicago
- baths 2
- rental type Condo
-
rates (USD)
$1
-
$1
/nt
- bedrooms 2
- sleeps 6
- community Lincoln Park/GoldCST
- baths 2
- rental type Condo
-
rates (USD)
$225
-
$375
/nt
$1,500 - $2,650 /wk
- bedrooms 2
- sleeps 6
- community
- baths 2
- rental type Condo
-
rates (USD)
$1
-
$1
/nt
- bedrooms 2
- sleeps 6
- community
- baths 2
- rental type Condo
-
rates (USD)
$1
-
$1
/nt
- bedrooms 2
- sleeps 6
- community
- baths 2
- rental type Condo
-
rates (USD)
$1
-
$1
/nt
- bedrooms 2
- sleeps 6
- community
- baths 2
- rental type Condo
-
rates (USD)
$1
-
$1
/nt
- bedrooms 2
- sleeps 8
- community
- baths 2½
- rental type Condo
-
rates (USD)
$1
-
$1
/nt
- bedrooms 3
- sleeps 6
- community
- baths 1½
- rental type Apartment
-
rates (USD)
$125
-
$185
/nt
$750 - $1,150 /wk
- bedrooms 3
- sleeps 8
- community Lake View/Roscoe Vil
- baths 2
- rental type Condo
-
rates (USD)
$950
-
$2,350
/wk
- bedrooms 3
- sleeps 8
- community Wicker Park
- baths 2
- rental type Condo
-
rates (USD)
$1
-
$1
/nt
- bedrooms 3
- sleeps 6
- community Gold Coast
- baths 2
- rental type Condo
-
rates (USD)
$215
-
$275
/nt
$1,350 - $1,800 /wk
$3,950 - $5,400 /mth
- bedrooms 3
- sleeps 8
- community East village
- baths 2½
- rental type Duplex
-
rates (USD)
$700
-
$1,800
/wk
- bedrooms 3
- sleeps 7
- community Ukrainian Village
- baths 2½
- rental type Townhome
-
rates (USD)
$200
-
$350
/nt
$1,200 - $1,500 /wk
$2,000 - $4,400 /mth
- bedrooms 3
- sleeps 8
- community
- baths 2½
- rental type Condo
-
rates (USD)
$1
-
$1
/nt
- bedrooms 3
- sleeps 8
- community
- baths 2½
- rental type Condo
-
rates (USD)
$1
-
$1
/nt
- bedrooms 3
- sleeps 40
- community
- baths 2½
- rental type Condo
-
rates (USD)
$325
-
$325
/nt
- bedrooms 4
- sleeps 8
- community Wrigleyville
- baths 2
- rental type Condo
-
rates (USD)
$1,750
-
$3,300
/wk
- bedrooms 4
- sleeps 10
- community
- baths 3
- rental type House
-
rates (USD)
$500
-
$1,000
/nt
$1,800 - $2,800 /wk
- bedrooms 4
- sleeps 12
- community
- baths 3
- rental type House
-
rates (USD)
$1
-
$1
/nt
- bedrooms 4
- sleeps 10
- community
- baths 3
- rental type Condo
-
rates (USD)
$1
-
$1
/nt
- bedrooms 4
- sleeps 10
- community Chicago
- baths 3½
- rental type House
-
rates (USD)
$1
-
$1
/nt
- bedrooms 4
- sleeps 9
- community Riverside Homes
- baths 3½
- rental type House
-
rates (USD)
$390
-
$490
/nt
$2,500 - $3,500 /wk
- bedrooms 4
- sleeps 14
- community Chicago
- baths 3½
- rental type House
-
rates (USD)
$1
-
$1
/nt
- bedrooms 4
- sleeps 10
- community Chicago
- baths 4
- rental type House
-
rates (USD)
$1
-
$1
/nt
- bedrooms 4
- sleeps 10
- community
- baths 4
- rental type House
-
rates (USD)
$1
-
$1
/nt
- bedrooms 4
- sleeps 10
- community Wrigleyville
- baths 4
- rental type House
-
rates (USD)
$1
-
$1
/nt
- bedrooms 5
- sleeps 18
- community
- baths 4½
- rental type House
-
rates (USD)
$4,800
-
$5,500
/wk
- bedrooms 6
- sleeps 14
- community Chicago
- baths 4½
- rental type House
-
rates (USD)
$1
-
$1
/nt
- bedrooms 6
- sleeps 12
- community Chicago
- baths 5
- rental type House
-
rates (USD)
$1
-
$1
/nt
- bedrooms 7
- sleeps 18
- community
- baths 5
- rental type House
-
rates (USD)
$1
-
$1
/nt
- bedrooms 15
- sleeps 40
- community
- baths 15
- rental type Condo
-
rates (USD)
$1
-
$1
/nt
