Vacation rentals near Maxwell Street Market
We found 3,712 vacation rentals — enter your dates for availability
Discover a selection of private vacation rentals close to Maxwell Street Market that can be your home away from home. Whether you're traveling with your kids or with friends, vacation rentals have the best amenities for hanging out with the people that matter most, which might include a fireplace and a washer and dryer. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.
Vacation rentals with weekly discounts - Maxwell Street Market
Showing deals for:Nov 14 - Nov 21
Image gallery for River North's Rock N' Roll - In The Heart of the City
9.69.6 out of 10 rating
Exceptional
(90 reviews)
River North's Rock N' Roll - In The Heart of the City
Chicago, IL
10% off
Price is CA $452
CA $452
CA $4,518 total
CA $4,518 total
includes taxes & fees
Image gallery for Beautiful, Remodeled Penthouse Unit in Old Town!
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Beautiful, Remodeled Penthouse Unit in Old Town!
Chicago, IL
5% off
Price is CA $432
CA $432
CA $4,369 total
CA $4,369 total
includes taxes & fees
Image gallery for Luxury Loft Collection 703 - Terrace - River North
1010 out of 10 rating
Exceptional
(16 reviews)
Luxury Loft Collection 703 - Terrace - River North
Chicago, IL
10% off
Price is CA $726
CA $726
CA $7,169 total
CA $7,169 total
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.29.2 out of 10 rating
Wonderful
(13 reviews)
3BR Luxury Modern Apartment
Chicago, IL
10% off
Price is CA $448
CA $448
CA $4,574 total
CA $4,574 total
includes taxes & fees
Image gallery for Chic Corner 2BR in the Loop | City & Lake Views
9.89.8 out of 10 rating
Exceptional
(52 reviews)
Chic Corner 2BR in the Loop | City & Lake Views
Chicago, IL
10% off
Price is CA $448
CA $448
CA $4,425 total
CA $4,425 total
includes taxes & fees
Image gallery for Michigan Ave 2BR: Balcony, Exclusive Access
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Michigan Ave 2BR: Balcony, Exclusive Access
Chicago, IL
10% off
Price is CA $508
CA $508
CA $5,132 total
CA $5,132 total
includes taxes & fees
Image gallery for Beautiful Corner 2 Bedroom in the Loop | Roof Deck
9.69.6 out of 10 rating
Exceptional
(58 reviews)
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
Chicago, IL
10% off
Price is CA $498
CA $498
CA $4,904 total
CA $4,904 total
includes taxes & fees
Image gallery for Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12 | Roof Deck
9.09.0 out of 10 rating
Wonderful
(15 reviews)
Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12 | Roof Deck
Chicago, IL
10% off
Price is CA $919
CA $919
CA $9,055 total
CA $9,055 total
includes taxes & fees
Image gallery for Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
1010 out of 10 rating
Exceptional
(6 reviews)
Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
Chicago, IL
10% off
Price is CA $231
CA $231
CA $2,692 total
CA $2,692 total
includes taxes & fees
Image gallery for Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
1010 out of 10 rating
Exceptional
(7 reviews)
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Whiting, IN
10% off
Price is CA $198
CA $198
CA $1,731 total
CA $1,731 total
includes taxes & fees
Image gallery for Cheerful 4 bedroom smart home w/ indoor fireplace
8.08.0 out of 10 rating
Very good
(14 reviews)
Cheerful 4 bedroom smart home w/ indoor fireplace
Chicago, IL
5% off
Price is CA $400
CA $400
CA $4,379 total
CA $4,379 total
includes taxes & fees
Image gallery for Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
9.89.8 out of 10 rating
Exceptional
(31 reviews)
Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, IL
10% off
Price is CA $330
CA $330
CA $3,295 total
CA $3,295 total
includes taxes & fees
Image gallery for Chic & Historic Apartment Steps from Mag Mile
9.89.8 out of 10 rating
Exceptional
(40 reviews)
Chic & Historic Apartment Steps from Mag Mile
Chicago, IL
10% off
Price is CA $153
CA $153
CA $1,722 total
CA $1,722 total
includes taxes & fees
Image gallery for Brownstone in Gold Coast - Downtown
9.89.8 out of 10 rating
Exceptional
(26 reviews)
Brownstone in Gold Coast - Downtown
Chicago, IL
20% off
Price is CA $129
CA $129
CA $1,489 total
CA $1,489 total
includes taxes & fees
Image gallery for Studio flat in the heart of Chicago's Gold Coast
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Studio flat in the heart of Chicago's Gold Coast
Chicago, IL
5% off
Price is CA $148
CA $148
CA $1,141 total
CA $1,141 total
includes taxes & fees
Image gallery for NEW LUXURY PENTHOUSE CONDO
1010 out of 10 rating
Exceptional
(186 reviews)
NEW LUXURY PENTHOUSE CONDO
Chicago, IL
5% off
Price is CA $366
CA $366
CA $3,820 total
CA $3,820 total
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(20 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
10% off
Price is CA $659
CA $659
CA $6,228 total
CA $6,228 total
includes taxes & fees
Image gallery for Spacious Home/King Bed/Fast Wi-Fi/Free Parking/Fenced Yard/Only 2 Steps to Enter
9.69.6 out of 10 rating
Exceptional
(49 reviews)
Spacious Home/King Bed/Fast Wi-Fi/Free Parking/Fenced Yard/Only 2 Steps to Enter
Worth, IL
7% off
Price is CA $284
CA $284
CA $2,625 total
CA $2,625 total
includes taxes & fees
Image gallery for Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
9.09.0 out of 10 rating
Wonderful
(7 reviews)
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Chicago, IL
10% off
Price is CA $178
CA $178
CA $1,831 total
CA $1,831 total
includes taxes & fees
Image gallery for Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
8.68.6 out of 10 rating
Excellent
(13 reviews)
Luxury Apartment in Bronzeville, Just Minutes from Downtown - RSV Now!
Chicago, IL
10% off
Price is CA $238
CA $238
CA $2,481 total
CA $2,481 total
includes taxes & fees
Image gallery for 3BR Prime Hyde Park Location Near University of Chicago and Dining
1010 out of 10 rating
Exceptional
(7 reviews)
3BR Prime Hyde Park Location Near University of Chicago and Dining
Chicago, IL
7% off
Price is CA $309
CA $309
CA $3,204 total
CA $3,204 total
includes taxes & fees
Image gallery for 1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
1010 out of 10 rating
Exceptional
(62 reviews)
1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier
Chicago, IL
10% off
Price is CA $435
CA $435
CA $4,307 total
CA $4,307 total
includes taxes & fees
Image gallery for Cozy 2BR/1BA Garden Apartment Near Lincoln Square
8.48.4 out of 10 rating
Very good
(11 reviews)
Cozy 2BR/1BA Garden Apartment Near Lincoln Square
Chicago, IL
10% off
Price is CA $108
CA $108
CA $1,745 total
CA $1,745 total
includes taxes & fees
Image gallery for Cozy 4-bedroom house in adorable Evanston with WiFi, AC
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Cozy 4-bedroom house in adorable Evanston with WiFi, AC
Evanston, IL
10% off
Price is CA $382
CA $382
CA $3,679 total
CA $3,679 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Maxwell Street Market
Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.49.4 out of 10
Exceptionalexceptional
470 reviews(470 reviews)
Level Chicago – Old Town
Sleeps 8
9.09.0 out of 10
Wonderfulwonderful
338 reviews(338 reviews)
The Neighborhood Hotel-Little Italy
Sleeps 4 · 1 bedroom
9.69.6 out of 10
Exceptionalexceptional
189 reviews(189 reviews)
Prime Location! Indoor Pool, Near Millenium Park, Shedd Aquarium, Willis Tower
Sleeps 2 · 1 bedroom · 1 bathroom
7.87.8 out of 10
Goodgood
83 reviews(83 reviews)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
877 reviews(877 reviews)
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sleeps 8 · 1 bedroom
7.87.8 out of 10
Goodgood
130 reviews(130 reviews)
Top rated rentals - Maxwell Street Market
Rooftop is perfect, great location
1010 out of 10
Exceptionalexceptional
186 reviews(186 reviews)
Spent 4 nights, we had everything we needed, plus nice extra touches. Location is central and close to some great neighborhoods. Jessica was very responsive and even accommodated an early check-in for a bit extra. Would definitely stay here again.
Alex P.
Stayed May 2024
Great place!
1010 out of 10
Exceptionalexceptional
295 reviews(295 reviews)
It was a great place to stay!!
Gordon S.
Stayed Mar 2020
Great Condo, Better Service
1010 out of 10
Exceptionalexceptional
117 reviews(117 reviews)
This property was amazing for a college buddies reunion trip. It was spacious, exactly as advertised, and had all the amenities you can ask for. The location is great and the check-in is a breeze. The host/owner, Carole, is an absolute pro and a joy to deal with.
Would definitely stay here again.
Aaron F.
Stayed Jun 2019
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value