Search results; Over 1,000 places in Old Town, Chicago

Prices include all fees
Guest favorite
Apartment in Old Town
Family-Friendly 2BD/2BA Prime Location (+parking)
6 beds
Jun 28 – Jul 3
R37,056 ZAR for 5 nights, originally R41,976 ZAR
for 5 nights
4.91 out of 5 average rating, 101 reviews
Superhost
Apartment in Chicago
Historic Old Town Flat - Minutes from Downtown!
1 double bed
Jun 15 – 20
R30,913 ZAR for 5 nights
for 5 nights
4.86 out of 5 average rating, 303 reviews
Superhost
Guest suite in Chicago
The Hidden Beach House
Free cancellation
Jul 6 – 11
R18,349 ZAR for 5 nights
for 5 nights
4.85 out of 5 average rating, 13 reviews
Superhost
Townhouse in Lincoln Park
Charming & Bright Multilevel Townhome with Parking
Free cancellation
Jul 19 – 24
R37,115 ZAR for 5 nights
for 5 nights
4.67 out of 5 average rating, 111 reviews
Guest favorite
Apartment in Lincoln Park
English garden apt. in the heart of Lincoln Park
2 beds
Jun 30 – Jul 5
R25,234 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 110 reviews
Superhost
Home in Chicago
Old Town Retreat
2 queen beds
Jun 6 – 11
R40,764 ZAR for 5 nights
for 5 nights
0 of 0 items showing
Page 1 of 3
Show more homes

More stays available for your dates

Condo in Near North Side
Old Town Penthouse. 6 Blocks to Historic Wells St.
6 beds
Jun 29 – Jul 4
R52,566 ZAR for 5 nights, originally R58,421 ZAR
for 5 nights
4.86 out of 5 average rating, 134 reviews
Superhost
Home in Old Town
Ideal Group Getaway: Best Location, Parking, Patio
Free cancellation
Jun 22 – 27
R52,863 ZAR for 5 nights
for 5 nights
Top guest favorite
Home in Lincoln Park
Top Floor in Historic Old Town!
3 beds
Aug 31 – Sep 5
R43,434 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 16 reviews
Superhost
Condo in Chicago
Chic Home! Walk to Nightlife-Comedy-Restaurants!
Free cancellation
Jul 21 – 26
R25,144 ZAR for 5 nights
for 5 nights
4.76 out of 5 average rating, 307 reviews
Guest favorite
Apartment in Lincoln Park
Cozy Lincoln Park Studio - Steps to Zoo!
Free cancellation
Jul 5 – 10
R18,735 ZAR for 5 nights
for 5 nights
4.84 out of 5 average rating, 274 reviews
Guest favorite
Home in Old Town
Extravagant Old Town Home w/ Sauna, Rooftop Lounge
Free cancellation
Aug 8 – 13
R159,329 ZAR for 5 nights, originally R173,233 ZAR
for 5 nights
4.98 out of 5 average rating, 58 reviews
Guest favorite
Home in Lincoln Park
Vintage Walk-up in Old Town
4 beds
Jun 8 – 13
R56,570 ZAR for 5 nights
for 5 nights
5.0 out of 5 average rating, 66 reviews
Superhost
Townhouse in Lincoln Park
Cheerful 3 story townhouse Old Town/LP
Free cancellation
Sep 3 – 8
R31,696 ZAR for 5 nights
for 5 nights
4.88 out of 5 average rating, 187 reviews
Guest favorite
Townhouse in Near North Side
Old Town/Lincoln Park Luxury Home Garage & Rooftop
Free cancellation
Aug 17 – 22
R62,927 ZAR for 5 nights
for 5 nights
4.94 out of 5 average rating, 129 reviews
Guest favorite
Apartment in Old Town
GROUP LUX in Old Town/Gold Coast (+private roof)
8 beds
Jun 28 – Jul 3
R84,644 ZAR for 5 nights
for 5 nights
4.97 out of 5 average rating, 38 reviews
Guest favorite
Home in Old Town
Luxury SOHO Styled Two-Level Townhouse | Old Town
Free cancellation
Aug 24 – 29
R89,410 ZAR for 5 nights, originally R107,681 ZAR
for 5 nights
4.94 out of 5 average rating, 103 reviews
Superhost
Apartment in Old Town
Old Town/Gold Coast Masterpiece (+private rooftop)
4 beds
Jun 28 – Jul 3
R41,697 ZAR for 5 nights
for 5 nights
4.84 out of 5 average rating, 79 reviews