50 Vacation Rentals In Chicago

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1. The Double Play, Wrigley Flats - Located Right next to Wrigley

Lincoln Park 200 m from Wrigley Field

# 1 out of 50 Vacation Rentals In Chicago

8.1

(295 reviews)

Facilities: Wifi, Pets Allowed

Apartment with 3 room options

$240 onwards

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2. The Avondale Guesthouse

Lincoln Park 3.1 kms from Wicker Park

# 2 out of 50 Vacation Rentals In Chicago

9.3

(137 reviews)

Facilities: Wifi, Bar, Pets Allowed, Garden, Food, Shuttle Service

Holiday home with only 1 room option

$180 onwards

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3. Luxéry Stay Chicago - Across from McCormick Place & Wintrust Arena

Michigan Avenue 100 m from Wintrust Arena

# 3 out of 50 Vacation Rentals In Chicago

8.8

(163 reviews)

Hotel Luxéry Stay Chicago is an excellent choice for visitors attending events at McCormick P (Read More)lace. The hotel offers clean and spacious rooms with modern amenities, and the staff is friendly and knowledgeable. The location is convenient, as it is connected to the convention center and offers beautiful views of the city skyline and Lake Michigan. There are also several nearby restaurants and attractions, including Chinatown. The hotel features a fitness center, laundry facility, and free WiFi. Overall, the hotel is a great choice, with guests recommending the hotel for its convenience and quality service.

4 star apartment with 7 room options

$231 onwards

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4. 2F Chicago's Little Italy near West Loop & Downtown

The Loop 500 m from Rush University

# 4 out of 50 Vacation Rentals In Chicago

9.4

(110 reviews)

Facilities: Wifi, Food

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5. Perfect place to enjoy the city or just relax

Chicago Chinatown 1.1 kms from Douglas Park

# 5 out of 50 Vacation Rentals In Chicago

8.9

(126 reviews)

Facilities: Wifi, Food

Apartment with only 1 room option

$180 onwards

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6. Forrestville Ave Large Suite

Michigan Avenue 2.6 kms from Guaranteed Rate Field

# 6 out of 50 Vacation Rentals In Chicago

9.1

(95 reviews)

Facilities: Wifi, Bar, Beach, Food

$110 onwards

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7. Adorable 2 bedroom with free street parking

Chicago Chinatown 1.1 kms from Douglas Park

# 7 out of 50 Vacation Rentals In Chicago

8.7

(99 reviews)

Facilities: Wifi

Apartment with only 1 room option

$300 onwards

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8. 1F Cozy Home in Little Italy near Downtown West Loop United Center

Downtown Chicago 500 m from Rush University

# 8 out of 50 Vacation Rentals In Chicago

9.8

(55 reviews)

Facilities: Wifi

Apartment with only 1 room option

$200 onwards

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9. Chicago Charm

Lincoln Park 2.2 kms from Loyola University Chicago

# 9 out of 50 Vacation Rentals In Chicago

9.7

(51 reviews)

Facilities: Wifi, Food

$213 onwards

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10. 1549 North Maplewood Avenue

Lincoln Park 1.1 kms from Wicker Park

# 10 out of 50 Vacation Rentals In Chicago

8.7

(77 reviews)

Facilities: Wifi, Bar, Food

Apartment with only 1 room option

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11. 2 Bed Apt w/ Office, Free Parking, Near Wrigley

Lincoln Park 800 m from Metro CHICAGO

# 11 out of 50 Vacation Rentals In Chicago

9.3

(55 reviews)

Facilities: Wifi, Food

$298 onwards

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12. The Blue Golden Luxury Modern 3- Bedroom Apartment in Chicago

Lincoln Park 2.1 kms from Northeastern Illinois University

# 12 out of 50 Vacation Rentals In Chicago

9.0

(61 reviews)

Facilities: Wifi, Food

Apartment with only 1 room option

$170 onwards

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13. Lincoln Park Gem

Lincoln Park 700 m from DePaul University

# 13 out of 50 Vacation Rentals In Chicago

8.9

(59 reviews)

Facilities: Wifi, Bar, Beach, Garden, Concierge Service

Apartment with only 1 room option

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14. Wrigley Oasis! Steps from the Field! - 3BD 1BA

Lincoln Park 400 m from Metro CHICAGO

# 14 out of 50 Vacation Rentals In Chicago

9.6

(39 reviews)

Facilities: Wifi, Pets Allowed, Food

$225 onwards

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15. Cozy Studio near Wrigley field and Boystown

Lincoln Park 1.1 kms from Metro CHICAGO

# 15 out of 50 Vacation Rentals In Chicago

8.7

(53 reviews)

Facilities: Wifi

Apartment with only 1 room option

$93 onwards

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16. Northside FAMLYNEST Lincoln Sq 4BR 2BA 2P Rare find

Lincoln Park 1.2 kms from North Park University

# 16 out of 50 Vacation Rentals In Chicago

9.8

(32 reviews)

Facilities: Wifi, Pets Allowed, Beach, Garden, Concierge Service, Food, Shuttle Service

$419 onwards

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17. Cozy 1 bedroom, 1 min from Irving Park Blue line, free parking

Lincoln Park 2.8 kms from North Park University

# 17 out of 50 Vacation Rentals In Chicago

8.7

(45 reviews)

Facilities: Wifi, Pets Allowed, Garden, Food

Apartment with only 1 room option

$97 onwards

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18. ✪ Cozy 1 Bedroom close to Downtown Chicago ✪

Old Town Chicago 1.2 kms from Wicker Park

# 18 out of 50 Vacation Rentals In Chicago

8.8

(42 reviews)

Facilities: Wifi

Apartment with only 1 room option

$133 onwards

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19. Lincoln Park Aparment with Backyard!

Lincoln Park 800 m from DePaul University

# 19 out of 50 Vacation Rentals In Chicago

9.1

(36 reviews)

Facilities: Wifi, Garden, Food

Apartment with only 1 room option

$98 onwards

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20. Spacious 5-BR Apt next to transit Free Parking

Chicago Chinatown 1.8 kms from Douglas Park

# 20 out of 50 Vacation Rentals In Chicago

8.8

(40 reviews)

Facilities: Wifi

$291 onwards

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21. Roscoe Village Guesthouse

Lincoln Park 2.1 kms from Metro CHICAGO

# 21 out of 50 Vacation Rentals In Chicago

9.0

(36 reviews)

Facilities: Wifi, Pets Allowed, Beach, Garden

Apartment with 13 room options

$113 onwards

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22. Trendy West Town Flat - 2 bed / 1.5 bath w parking

Old Town Chicago 1.6 kms from United Center

# 22 out of 50 Vacation Rentals In Chicago

9.4

(29 reviews)

Facilities: Wifi

$220 onwards

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23. Lincoln Park 3 BR Penthouse

Lincoln Park 700 m from DePaul University

# 23 out of 50 Vacation Rentals In Chicago

9.0

(33 reviews)

Reviewers Mention: The tenants at 1200 W Webster are highly recommended due to their remarkab (Read More)le looks, charming personalities, and dignified attitudes. They are compared to Homer's Sirens, Leonardo da Vinci's Vetruvian Man, Michelangelo's David, and Mufasa from The Lion King. Attending one of their soirees is promised to be a memorable experience.

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24. Superior

Old Town Chicago 1.8 kms from United Center

# 24 out of 50 Vacation Rentals In Chicago

9.4

(28 reviews)

Facilities: Wifi, Garden

$275 onwards

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25. Granville appartment

Lincoln Park 2.2 kms from Northeastern Illinois University

# 25 out of 50 Vacation Rentals In Chicago

8.6

(36 reviews)

Facilities: Wifi, Food, Shuttle Service

Apartment with only 1 room option

$118 onwards

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26. McCormick Place modern loft with an amazing city skyline view and optional parking for 8 guests

Michigan Avenue 300 m from Wintrust Arena

# 26 out of 50 Vacation Rentals In Chicago

8.8

(33 reviews)

Facilities: Wifi, Bar, Pets Allowed

$324 onwards

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27. My Cozy Heavon

Lincoln Park 1.1 kms from Wicker Park

# 27 out of 50 Vacation Rentals In Chicago

8.4

(38 reviews)

Facilities: Wifi, Food

Apartment with only 1 room option

$148 onwards

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28. Ethan Golden LLC

Chicago Chinatown

# 28 out of 50 Vacation Rentals In Chicago

8.1

(43 reviews)

Facilities: Pets Allowed

Apartment with only 1 room option

$130 onwards

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29. Rustic Mix

Chicago Chinatown 2.0 kms from Douglas Park

# 29 out of 50 Vacation Rentals In Chicago

9.0

(26 reviews)

Facilities: Wifi

Apartment with only 1 room option

$219 onwards

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30. The Neighborhood Hotel Lincoln Park

Lincoln Park 1.1 kms from DePaul University

# 30 out of 50 Vacation Rentals In Chicago

8.9

(25 reviews)

Facilities: Wifi, Food

4 star apartment with 14 room options

$237 onwards

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31. Irving Park/Avondale updated vintage top unit 2-flat

Lincoln Park 2.3 kms from North Park University

# 31 out of 50 Vacation Rentals In Chicago

9.8

(18 reviews)

Facilities: Wifi, Pets Allowed

Apartment with only 1 room option

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32. Ethan 3 rooms

Chicago Chinatown

# 32 out of 50 Vacation Rentals In Chicago

8.3

(30 reviews)

Facilities: Wifi, Pets Allowed

Apartment with only 1 room option

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33. Historic Oak Park Home for 6 / Hemingway District

9.1 kms from Douglas Park

# 33 out of 50 Vacation Rentals In Chicago

9.2

(21 reviews)

Facilities: Wifi

Apartment with only 1 room option

$271 onwards

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34. Casa Cerca De La Playa

Michigan Avenue 3.3 kms from Stony Island Arts Bank

# 34 out of 50 Vacation Rentals In Chicago

8.7

(25 reviews)

Facilities: Wifi, Bar, Beach, Garden, Food

Apartment with only 1 room option

$232 onwards

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35. Stunning Condo #2 - Downtown River North

Downtown Chicago 900 m from Clark/Division Station

# 35 out of 50 Vacation Rentals In Chicago

9.3

(20 reviews)

Facilities: Wifi

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36. 15 min Ohare/Rivers Casino/Downtown & Parking1

4.5 kms from Northeastern Illinois University

# 36 out of 50 Vacation Rentals In Chicago

7.4

(43 reviews)

Facilities: Wifi, Garden

Apartment with only 1 room option

$131 onwards

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37. CoWorking Gym Pool Golfsim Steps from FultonMarket by Cloud9-160

The Loop 500 m from wndr museum

# 37 out of 50 Vacation Rentals In Chicago

9.2

(20 reviews)

Facilities: Wifi, Pets Allowed, Pool, Garden

4 star apartment with 6 room options

$396 onwards

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38. Modern 2 Bedroom in Avondale

Lincoln Park 4.1 kms from North Park University

# 38 out of 50 Vacation Rentals In Chicago

9.0

(21 reviews)

Facilities: Wifi

Apartment with only 1 room option

$217 onwards

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39. Couture Themed 3 Bedroom in Prime Spot with Patio, Parking, Fireplace, Pets Welcome

Old Town Chicago 600 m from Clark/Division Station

# 39 out of 50 Vacation Rentals In Chicago

8.4

(26 reviews)

Facilities: Wifi, Bar, Pets Allowed, Beach, Garden, Food

$279 onwards

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40. Immaculate Brand New Condo Downtown

The Loop 500 m from United Center

# 40 out of 50 Vacation Rentals In Chicago

9.2

(19 reviews)

Facilities: Wifi

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41. McCormick Place 2br-2ba with Optional Parking, Patio, Gym access for 6 guests

Michigan Avenue 300 m from Wintrust Arena

# 41 out of 50 Vacation Rentals In Chicago

8.3

(26 reviews)

Reviewers Mention: The McCormick Place convention center is praised for its large spaces, con (Read More)venient location, and friendly staff. It is described as a fantastic venue for events and trade shows, with a spacious conference area and easy transportation options. The facilities are clean and well-maintained, although some mention the need for bathroom upgrades. The car show held at the center is highly recommended, with impressive displays and excellent organization. The availability of parking and a gym is also appreciated. However, there are limited food options and a lot of walking involved. Overall, it is a popular choice for events and exhibitions.

$300 onwards

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