Chicago vacation rentals

We have a choice of 735 vacation home rentals in Chicago. Find a variety of accommodation options in Chicago Loop, Lakeview and Downtown Chicago districts or close to Dearborn Station to feel the urban vibe. Enter your details and booked.net will find accommodation where you can enjoy your stay after exploring Chicago.
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Handpicked vacation rentals in Chicago

When on city escape, all you need is a nice apartment to relax and enjoy your time off work. We can suggest townhouses, apartments, waterfront cabins in Chicago for you. Find accommodation which suits you the most and get it booked!
Stay Alfred At The Seneca photos Exterior
8.6
GreatBased on139 reviews
18
Stay Alfred At The Seneca
200 E Chestnut St, Chicago
from US$  126
Millennium Park Apartments photos Exterior
6.4
NiceBased onreviews
38
Millennium Park Apartments
55 E Washington St., Chicago
from US$  196
The Penthouse At Grand Plaza photos Exterior
9.2
PerfectBased onreviews
58
The Penthouse At Grand Plaza
540 North State Street, Chicago
from US$  383
Chicago Grand Plaza Suites photos Room
50
Chicago Grand Plaza Suites
540 North State Street, Chicago
from US$  152
Modern Loop Apartments photos Exterior
60
Modern Loop Apartments
215 West Washington, Chicago
from US$  181
Mda City Apartments photos Interior
17
Mda City Apartments
63 East Lake Street, Chicago
from US$  127
215 West Luxury Apartments photos Room
35
215 West Luxury Apartments
215 West Washington , Chicago
0
Charming 4Br In Lincoln Park By Sonder
N Orchard And W Wrightwood Ave., Chicago
Mccormick Place Guest House photos Exterior
54
Mccormick Place Guest House
3643 South Indiana Avenue, Chicago
from US$  226
Global Luxury Suites In Downtown Chicago photos Exterior
24
Global Luxury Suites In Downtown Chicago
111 W Wacker Drive, Chicago

Exclusive luxury places to stay in Chicago

You will enjoy the opulent atmosphere of comfortable vacation homes in Chicago. Spend your summer vacation at one of the city's most luxury places. With just a few clicks you'll get the most exclusive place to stay in Chicago.
Stay Alfred At Park Michigan photos Exterior
52
Stay Alfred At Park Michigan
1212 S Michigan Avenue, Chicago
from US$  593
West Loop Lofts photos Exterior
24
West Loop Lofts
1650 W Adams St, Chicago
from US$  378
Apartment In River North With Balcony photos Exterior
30
Apartment In River North With Balcony
750 North Hudson Avenue, Chicago
from US$  364
Stay Alfred On State Street photos Exterior
25
Stay Alfred On State Street
540 N State Street, Chicago
from US$  299
Furnished Suites In South Loop Chicago photos Exterior
26
Furnished Suites In South Loop Chicago
1333 S Wabash Ave, Chicago
from US$  217
Oakwood 200 Squared photos Exterior
29
Oakwood 200 Squared
210 North Wells Street, Chicago
from US$  205
Chicago Guest House On Lakewood Avenue photos Exterior
73
Chicago Guest House On Lakewood Avenue
3715 N Lakewood Avenue, Chicago
from US$  195
Pampered Rest Stop 3 Br photos Exterior
18
Pampered Rest Stop 3 Br
5011 South Central Avenue Second Floor, Chicago
from US$  189
Lang House Bed & Breakfast photos Exterior
71
Lang House Bed & Breakfast
7421 N. Sheridan Rd., Chicago
from US$  179
Magnolia Studios photos Exterior
30
Magnolia Studios
5705 N Magnolia Ave, Chicago
from US$  147

High graded cheap vacation homes in Chicago

A penny saved is a penny earned. It is not necessary to tighten your belt to afford a nice vacation home in Chicago. Our team has checked available dates in United States received from 100+ providers and filtered nice vacation rentals in Chicago to find the best options according to your budget. Surf through!
Pilsen Roadhouse photos Exterior
25
Pilsen Roadhouse
1827 S Racine Ave, Chicago
from US$  112
Millennium Park Experience At Indiana Place photos Exterior
15
Millennium Park Experience At Indiana Place
4032 South Indiana Avenue, Chicago
from US$  109
Sunny & Updated Vintage 2Br 1Ba photos Exterior
17
Sunny & Updated Vintage 2Br 1Ba
1260 West Victoria Street, Chicago
from US$  105
Bohemian House Near Downtown Chicago photos Exterior
24
Bohemian House Near Downtown Chicago
2822 West Cermak Road, Chicago
from US$  99
Dch 215 Lake photos Exterior
28
Dch 215 Lake
215 West Lake Street, Chicago
from US$  95
May Street Apartel photos Exterior
22
May Street Apartel
747 North May Street, Chicago
from US$  80
Ich Suites photos Exterior
56
Ich Suites
215 West Washington Street, Chicago
from US$  80
Mccormick Place Experience At Indiana Place photos Exterior
11
Mccormick Place Experience At Indiana Place
4032 South Indiana Avenue, Chicago
from US$  76
Farwell Dream photos Exterior
49
Farwell Dream
1509 West Farwell Avenue, Chicago
from US$  48
Hollywood Sensation Home photos Exterior
36
Hollywood Sensation Home
1656 West Hollywood Avenue, Chicago
from US$  36
SHOW ALL 284 VACATION RENTALS IN Chicago

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