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!
Pittsfield Apartments + Suites photos Room
6.4
NiceBased onreviews
42
Pittsfield Apartments + Suites
55 E Washington St., Chicago
from US$  150
Stay Alfred At The Seneca photos Room
8.6
GreatBased on139 reviews
18
Stay Alfred At The Seneca
200 East Chestnut Street, Chicago
from US$  126
Steps To Everything Wrigleyville Suite Id #50 photos Exterior
13
Steps To Everything Wrigleyville Suite Id #50
655 Irving Park Rd, Chicago
from US$  665
Mccormick Place Guest House photos Exterior
54
Mccormick Place Guest House
3643 South Indiana Avenue, Chicago
from US$  122
Navy Pier Suite, Id # 31 photos Exterior
6
Navy Pier Suite, Id # 31
440 Mcclurg Ct, Chicago
from US$  692
House 5863 photos Interior
9.6
PerfectBased onreviews
33
House 5863
5863 North Glenwood , Chicago
Steps To Everything - Navy Pier Suite, Id #30 photos Exterior
26
Steps To Everything - Navy Pier Suite, Id #30
480 Mcclurg Ct, Chicago
from US$  612
Mda City Apartments photos Interior
17
Mda City Apartments
63 East Lake Street, Chicago
from US$  127
Lang House Bed & Breakfast photos Exterior
70
Lang House Bed & Breakfast
7421 N. Sheridan Rd., Chicago
from US$  179
Oakwood Millennium Park Plaza photos Exterior
6.6
NiceBased onreviews
18
Oakwood Millennium Park Plaza
151 North Michigan Avenue, 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.
Chicago Grand Plaza Suites photos Room
75
Chicago Grand Plaza Suites
540 North State Street, Chicago
from US$  256
Wicker Park Bathhouse Apartments photos Exterior
18
Wicker Park Bathhouse Apartments
1914 West Division, Chicago
from US$  442
Grand Local Ave photos Exterior
42
Grand Local Ave
1411 W Grand Ave, Chicago
from US$  263
Luxury At Lakeshore East photos Room
13
Luxury At Lakeshore East
345 East Wacker Drive, Chicago
from US$  187
Oakwood 200 Squared photos Exterior
29
Oakwood 200 Squared
210 North Wells Street, Chicago
from US$  240
Global Luxury Apartments In Chicago photos Room
35
Global Luxury Apartments In Chicago
215 West Washington St., Chicago
Chicago Guest House On Henderson Street photos Exterior
35
Chicago Guest House On Henderson Street
1330 West Henderson Street, Chicago
from US$  236
Chicago Guest House On Newport photos Exterior
58
Chicago Guest House On Newport
1216 West Newport Avenue, Chicago
from US$  408
Chicago Guest House On Lakewood Avenue photos Exterior
73
Chicago Guest House On Lakewood Avenue
3715 N Lakewood Avenue, Chicago
from US$  354
30 East Huron Chicago photos Room
34
30 East Huron Chicago
30 East Huron Street, Chicago
from US$  185

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!
Ginosi Basics Loop Apartel photos Exterior
17
Ginosi Basics Loop Apartel
417 South Dearborn Street, Chicago
from US$  441
Corporate Suites In The Heart Of Magnificent Mile photos Exterior
32
Corporate Suites In The Heart Of Magnificent Mile
East Grand Avenue & North St Clair Street, Chicago
from US$  256
Chicago Hideaway photos Exterior
16
Chicago Hideaway
2942 West Belle Plaine Avenue 1E, Chicago
from US$  163
Corporate Suites Network - 845 N State photos Exterior
27
Corporate Suites Network - 845 N State
845 North State Street, Chicago
from US$  201
2142 West Walton Apartment photos Exterior
30
2142 West Walton Apartment
2142 West Walton, Chicago
from US$  328
Apartments On N Southport Avenue photos Exterior
29
Apartments On N Southport Avenue
3707 N Southport Ave #2, Chicago
from US$  242
Near South Side Apartment photos Exterior
21
Near South Side Apartment
512 West 37Th Street, Chicago
from US$  172
Convention Center Area Apartment photos Exterior
28
Convention Center Area Apartment
512 West 37Th Street, Chicago
from US$  184
Pilsen Roadhouse photos Exterior
25
Pilsen Roadhouse
1827 S Racine Ave, Chicago
from US$  120
Royal Living Group Union Station photos Exterior
75
Royal Living Group Union Station
601 W Jackson Blvd, Chicago
from US$  470
SHOW ALL 710 VACATION RENTALS IN Chicago

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Aquarium III