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Far Southeast Side Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Far Southeast Side holiday rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,192 reviews)
"Great location"
United States
JAVIER
The price is HK$1,366
HK$1,833 total
includes taxes & fees
5 Jul - 6 Jul
Sentral Michigan Avenue
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (495 reviews)
The price is HK$1,982
HK$2,520 total
includes taxes & fees
29 Jun - 30 Jun
Level Chicago – Old Town
Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (13 reviews)
"Un superbe building avec des prestations sympas, un chouette appartement avec tout ce qu’il faut pour être confortable et les petits détails qui font la différence, notamment pour un court séjour car cela évite de voyager avec ou de courir en acheter: savon pour les mains, shampooing, gel douche, lessive, café etc il est très proche de la ligne rouge du métro et d’un arrêt de bus. "
United States
Emeline B.
The price is HK$2,649
HK$5,658 total
includes taxes & fees
8 Jul - 9 Jul
ENVITAE Hotel, 4BR Luxury Modern Apartments
Fridge, microwave, oven, stovetop

River North Rooftop With In and Out Parking 5

River North Rooftop With In and Out Parking 5
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"Everything was amazing, property was even better than expected"
United States
Jacob
The price is HK$2,218
HK$4,483 total
includes taxes & fees
9 Jul - 10 Jul
River North Rooftop With In and Out Parking 5
Desk, iron/ironing board, travel cot, WiFi

Gold Coast Hideaway | Vintage & Inviting Studio

Gold Coast Hideaway | Vintage & Inviting Studio
Downtown Chicago
The price is HK$940
HK$1,765 total
includes taxes & fees
30 Jun - 1 Jul
Gold Coast Hideaway | Vintage & Inviting Studio
TV, offices

LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
The price is HK$1,309
HK$1,759 total
includes taxes & fees
21 Jun - 22 Jun
LIVN Millennium Park Downtown Chicago 1 BR
TV, offices

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Great stay."
United States
Mollie A.
The price is HK$1,434
HK$4,730 total
includes taxes & fees
7 Jul - 8 Jul
Modern West Loop Gem-City Views & Prime Location 5
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is HK$2,077
HK$4,710 total
includes taxes & fees
1 Jul - 2 Jul
River North Rooftop With In and Out Parking 3
TV, offices

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Clean spacious great location easy to get everywhere "
United States
Melissa M.
The price is HK$1,654
HK$2,844 total
includes taxes & fees
6 Jul - 7 Jul
Chicago-Themed 1BR in a Central Spot near Downtown
1 bedroom, iron/ironing board, travel cot, WiFi

LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Excellent stay. Great area and very happy with everything"
United States
Abigail B.
The price is HK$1,364
HK$1,833 total
includes taxes & fees
21 Jun - 22 Jun
LIVN West Loop Chicago Classic Queen Studio
Interior

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
The price is HK$4,216
HK$7,843 total
includes taxes & fees
9 Jul - 10 Jul
Premium Urban 4BR - Perfect Mix of Comfort & Location
1 bedroom, iron/ironing board, travel cot, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.2 out of 10, Wonderful, (12 reviews)
"The host was great at communicating and the apartment was very clean! "
United States
Hannah C.
The price is HK$1,238
HK$2,280 total
includes taxes & fees
30 Jun - 1 Jul
West Loop Living – Bright 1BR
TV, offices

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
8.0 out of 10, Very good, (3 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is HK$1,199
HK$2,253 total
includes taxes & fees
21 Jun - 22 Jun
Sunlit 1BR Apartment | Warm & Welcoming Space
TV, offices

Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago Stay with Free In & Out Parking 5
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"This VRBO was perfect for our family as we visited our college student in downtown Chicago. Plenty of space, sparkling clean, comfy beds. Only two things that I think could be improved/better communicated: only one key card is provided, and the beds are full size not queen (but they were SUPER comfortable!!!)"
United States
Gina C.
The price is HK$1,849
HK$4,400 total
includes taxes & fees
7 Jul - 8 Jul
Downtown Chicago Stay with Free In & Out Parking 5
TV, offices

3BR Luxury Suite w/Gym and Balcony

3BR Luxury Suite w/Gym and Balcony
Downtown Chicago
9.4 out of 10, Exceptional, (30 reviews)
"A wonderful place to stay and everything was so perfect! Could not recommend staying here enough! "
United States
Cassidy L.
The price is HK$2,908
HK$5,996 total
includes taxes & fees
1 Jul - 2 Jul
3BR Luxury Suite w/Gym and Balcony
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.8 out of 10, Excellent, (3 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$1,238
HK$2,280 total
includes taxes & fees
30 Jun - 1 Jul
1BR Modern Luxe Apt with In-Unit Laundry
Interior

Beautiful Rustic Cabin for Two!

Beautiful Rustic Cabin for Two!
Griffith
8.6 out of 10, Excellent, (29 reviews)
"The cabin was cute and cozy and the host was very welcoming. "
United States
Deric D.
The price is HK$650
HK$904 total
includes taxes & fees
20 Jun - 21 Jun
Beautiful Rustic Cabin for Two!
2 bedrooms, iron/ironing board, travel cot, WiFi

Sunlit & Chic 2BR Retreat

Sunlit & Chic 2BR Retreat
Hyde Park
10.0 out of 10, Exceptional, (4 reviews)
"Wonderful condo! Very clean and great location! We enjoyed our stay very much."
United States
Misty H.
The price is HK$1,129
HK$2,278 total
includes taxes & fees
8 Jul - 9 Jul
Sunlit & Chic 2BR Retreat
Hair dryer, towels, soap, toilet paper

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (83 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is HK$776
HK$1,441 total
includes taxes & fees
21 Jun - 22 Jun
Cozy studio in Andersonville Chicago
Pool

South Loop Rooftop With In and Out Parking 2

South Loop Rooftop With In and Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay! Parking was easy and secure. The building was super clean and had lots of amenities. Host was very responsive to messages and very accommodating to our last minute schedule changes. "
United States
Kara V.
The price is HK$2,978
HK$6,045 total
includes taxes & fees
17 Jul - 18 Jul
South Loop Rooftop With In and Out Parking 2
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Far Southeast Side Hotel Reviews

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"It was in walking distance of everything"
Deborrah 2-night trip
Posted less than an hour ago
Eurostars Magnificent Mile

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