Old Town, Chicago vacation rentals

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Top-rated vacation rentals in Old Town, Chicago

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Townhouse in Lincoln Park

4.98 out of 5 average rating, 224 reviews

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit

The newly renovated spacious apartment is furnished with brand new modern king bed in the bedroom to ensure restful nights. In large living room, beautiful cherry dining table to enjoy morning coffee and comfortable L-shape leather sofa for watching your favorite movies from Netflix on 43" flat screen TV. The brand new fully equipped kitchen has a granite countertops, stainless steel appliances. The modern marble bathroom has a huge mirror over the sink, glass sliding shower doors, a full size bath tub and a hair dryer. Spacious 3 room apartment with all the amenities specified above is for guests use only and free residential parking permits provided upon request. I'm always available. I live on the 2nd floor of the townhouse with my husband and work at a bridal boutique which I own on west Armitage Ave. The apartment is super conveniently located in the Armitage/Sheffield. It's 2 1/2 blocks or 5 minutes walk to both Brown and Red line stations which make getting around Chicago fast and easy. Visiting lake front Millennium Park takes less than 20 minutes from the apartment. My neighborhood is surrounded by Old Town, full of local shops and restaurants, Wrigley Field, eclectic Bucktown shops, and the Lincoln Park Zoo. The 3 Michelin-starred restaurant, Alinea is 2-minute walk from the door. Take either Red ( North/Clybourn ) or Brown (Armitage/Sheffield ) line for exploring Rush st( 1 stop) Water Tower, Michigan Ave, Mag miles, Gold Coast( 2 stops ) The Navy Pier( 3 stops) Millennium Park, Cloud Gate/ The Bean, Buckingham Fountain, Art Institute of Chicago,( 4stops). Both stations are within 5 min walking distance from the apartment. It's also a short cab or Uber ride to Michigan Ave. Gold Coast. No smoking, no street shoes, no parties allowed. The nightly rates are for 2 guests only and $25 guest fee applys for 3rd guest. There is a $500.00 penalty for breaking the each rule.

Dec 18 – 25

R4,073 ZAR per night
Guest favorite

Apartment in Lincoln Park

4.98 out of 5 average rating, 293 reviews

Redesigned Lower Level Studio in Historic Building

The space is very comfortable, quiet and cozy. There are new cabinets, granite counter tops, all new appliances and a washer and dryer. Guests sleep on a king size tempur-pedic mattress or a queen size trundle style pull out sofa. There is hi-speed wi-fi, cable TV (Showtime), 55' flat screen TV and a wood burning fireplace. The bathroom is immaculate and includes a full bathtub with shower. This is a private apartment and you will have access to the entire suite. There is a back and front door with adequate lighting and easy access for guests. My family and I live next door and I will be available at our guests convenience. I am happy to provide any information, recommendations, directions etc.. I am easy to reach and am always available but will not intrude on our guests privacy. This unit is on a beautiful tree lined street in the heart of Old Town, close to St. Michael's Church, Steppenwolf Theater, and the Second City Improv Theater. The location allows for easy access to all of Chicago by either train, bus, or car. The blue and brown line train stations are within walking distance. Street parking is readily available and no permits are necessary. A Chicago Cab or Uber can get you to Milleniumm Park in approx. 15 minutes. Four adults can comfortably stay in this unit. The king size tempur_pedic mattress is the pinnacle of comfort and the queen size trundle style pull out sofa is comparable to sleeping on an actual queen size mattress. The queen size bed could comfortably fit 3 children. There is street parking readily available but I can provide an assigned space behind the building if necessary, for additional cost.

Apr 29 – May 6

R2,981 ZAR per night
Guest favorite

Apartment in Lincoln Park

4.99 out of 5 average rating, 191 reviews

Explore Lincoln Park from a Polished Apartment

This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Jan 22 – 29

R3,154 ZAR per night

Popular amenities for Old Town, Chicago vacation rentals

Stay near Old Town, Chicago's top sights

The Second City433 locals recommend
Hotel Lincoln30 locals recommend
Newcity12 locals recommend
Alinea98 locals recommend
Zanies Comedy Night Club77 locals recommend
Summer House Santa Monica118 locals recommend

Other great vacation rentals in Old Town, Chicago

Superhost

Condo in West Town

4.87 out of 5 average rating, 433 reviews

Humboldt Park Traveler's Lodge

Apr 5 – 12

R1,731 ZAR per night
Guest favorite

Apartment in Lincoln Park

4.91 out of 5 average rating, 137 reviews

Chicago Lincoln Park North Pond 2 Bedroom Pied-à-Terre

Dec 2 – 9

R3,201 ZAR per night
Guest favorite

Apartment in Old Town

4.91 out of 5 average rating, 153 reviews

OLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)

Jun 7 – 14

R10,452 ZAR per night
Guest favorite

Guest suite in Lincoln Square

5.0 out of 5 average rating, 290 reviews

Private Lincoln Square one bed+bath studio apt.

Sep 16 – 23

R2,658 ZAR per night
Guest favorite

Guest suite in Lincoln Square

4.91 out of 5 average rating, 416 reviews

Cozy, Quiet, Garden Getaway!

Jan 7 – 14

R1,947 ZAR per night
Guest favorite

Apartment in Lincoln Park

4.89 out of 5 average rating, 138 reviews

Lincoln Paradise– Steps to Park & Zoo!

Nov 29 – Dec 6

R4,314 ZAR per night
Guest favorite

Apartment in Lincoln Park

4.87 out of 5 average rating, 190 reviews

New! Beautiful 2BR Apartment in Old Town

Oct 1 – 8

R4,769 ZAR per night
Guest favorite

Apartment in Wicker Park

4.95 out of 5 average rating, 171 reviews

Wicker Park/Bucktown Location

Jun 18 – 25

R2,277 ZAR per night
Guest favorite

Apartment in West Town

4.96 out of 5 average rating, 260 reviews

Turquoise Wonder - Clean, Cozy & Stylish Apt

Nov 17 – 24

R1,852 ZAR per night
Guest favorite

Apartment in Near North Side

4.98 out of 5 average rating, 174 reviews

Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D

Apr 29 – May 4

R3,389 ZAR per night
Guest favorite

Apartment in Roscoe Village

4.96 out of 5 average rating, 235 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

Oct 16 – 23

R1,982 ZAR per night
Superhost

Condo in Lincoln Park

4.8 out of 5 average rating, 80 reviews

Stylish Stay Steps from Old Town + Lincoln Park

Dec 14 – 21

R2,707 ZAR per night

Other great vacation rentals in Old Town, Chicago

Guest favorite

Guest suite in Old Town

4.99 out of 5 average rating, 73 reviews

Travelers Retreat in Old Town Chicago

Jun 18 – 25

R3,512 ZAR per night
Guest favorite

Home in Lincoln Park

5.0 out of 5 average rating, 39 reviews

Charming 3-BED in Lincoln Park/ Old Town & Parking

Oct 26 – Nov 2

R4,188 ZAR per night
Guest favorite

Apartment in Lincoln Park

4.97 out of 5 average rating, 67 reviews

English garden apt. in the heart of Lincoln Park

Aug 9 – 16

R3,839 ZAR per night
Guest favorite

Apartment in Old Town

4.94 out of 5 average rating, 51 reviews

Breathtaking & Chic Oasis Loc in Desirable Old Twn

Jul 24 – 31

R7,439 ZAR per night
Guest favorite

Guest suite in West Loop

4.95 out of 5 average rating, 76 reviews

Cozy one-bedroom suite in the heart of West Loop

Dec 10 – 17

R2,659 ZAR per night
Guest favorite

Apartment in Old Town

4.93 out of 5 average rating, 74 reviews

OLD TOWN GARDEN GETAWAY

Apr 23 – 30

R3,727 ZAR per night
Guest favorite

Apartment in Lincoln Park

4.9 out of 5 average rating, 39 reviews

Entire Apartment in Lincoln Park

Nov 21 – 28

R3,599 ZAR per night
Guest favorite

Condo in Old Town

4.95 out of 5 average rating, 19 reviews

Two Floor Luxury 3 Bedroom Condo in Old Town

Dec 14 – 21

R5,109 ZAR per night
Guest favorite

Home in Lincoln Park

5.0 out of 5 average rating, 34 reviews

Vintage Walk-up in Old Town

Apr 22 – 29

R6,277 ZAR per night
Superhost

Apartment in Lincoln Park

4.83 out of 5 average rating, 46 reviews

Cozy Lincoln Park Studio - Across from Zoo!

Apr 8 – 15

R2,559 ZAR per night
Guest favorite

Condo in Lincoln Park

5.0 out of 5 average rating, 11 reviews

Old Town Gem

Nov 25 – Dec 2

R6,816 ZAR per night
Guest favorite

Apartment in Lincoln Park

4.98 out of 5 average rating, 91 reviews

Elegant Depaul Apt on Jonquil Park

Jan 23 – 30

R2,618 ZAR per night

Quick stats about vacation rentals in Old Town, Chicago

Total rentals

80 properties

Rentals with dedicated workspaces

40 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

50 properties are a good fit for families

Total number of reviews

6.1K reviews

Nightly prices starting at

R1,138 ZAR before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Old Town