50 Vacation Rentals In Chicago

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1. The Double Play, Wrigley Flats - Cubs! - Located Right next to Wrigley and Transit

Lincoln Park 200 m from Wrigley Field

# 1 out of 50 Vacation Rentals In Chicago

8.2

(291 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

(132 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

(155 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

9.5

(102 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

8.8

(117 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

9.2

(89 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

8.6

(92 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

(48 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

9.8

(45 reviews)

Facilities: Wifi, Food

$213 onwards

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

Lincoln Park 2.1 kms from Northeastern Illinois University

# 10 out of 50 Vacation Rentals In Chicago

9.0

(60 reviews)

Facilities: Wifi, Food

Apartment with only 1 room option

$170 onwards

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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

9.2

(47 reviews)

Facilities: Wifi, Food

$298 onwards

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

Lincoln Park 400 m from Metro CHICAGO

# 12 out of 50 Vacation Rentals In Chicago

9.6

(39 reviews)

Facilities: Wifi, Pets Allowed, Food

$225 onwards

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13. Cozy Studio near Wrigley field and Boystown

Lincoln Park 1.1 kms from Metro CHICAGO

# 13 out of 50 Vacation Rentals In Chicago

8.7

(51 reviews)

Facilities: Wifi

Apartment with only 1 room option

$93 onwards

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14. Lincoln Park Aparment with Backyard!

Lincoln Park 800 m from DePaul University

# 14 out of 50 Vacation Rentals In Chicago

9.1

(39 reviews)

Facilities: Wifi, Garden, Food

Apartment with only 1 room option

$98 onwards

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

Lincoln Park 1.2 kms from North Park University

# 15 out of 50 Vacation Rentals In Chicago

9.8

(30 reviews)

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

$419 onwards

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

Lincoln Park 2.8 kms from North Park University

# 16 out of 50 Vacation Rentals In Chicago

8.7

(44 reviews)

Facilities: Wifi, Pets Allowed, Garden, Food

Apartment with only 1 room option

$97 onwards

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17. ✪ Cozy 1 Bedroom close to Downtown Chicago ✪

Old Town Chicago 1.2 kms from Wicker Park

# 17 out of 50 Vacation Rentals In Chicago

8.9

(40 reviews)

Facilities: Wifi

Apartment with only 1 room option

$133 onwards

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

Chicago Chinatown 1.8 kms from Douglas Park

# 18 out of 50 Vacation Rentals In Chicago

8.8

(41 reviews)

Facilities: Wifi

$291 onwards

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19. My Cozy Heavon

Lincoln Park 1.1 kms from Wicker Park

# 19 out of 50 Vacation Rentals In Chicago

8.7

(36 reviews)

Facilities: Wifi, Food

Apartment with only 1 room option

$148 onwards

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

Old Town Chicago 1.6 kms from United Center

# 20 out of 50 Vacation Rentals In Chicago

9.5

(26 reviews)

Facilities: Wifi

$220 onwards

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21. Ethan Golden LLC

Chicago Chinatown

# 21 out of 50 Vacation Rentals In Chicago

8.2

(42 reviews)

Facilities: Pets Allowed

Apartment with only 1 room option

$130 onwards

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22. Roscoe Village Guesthouse

Lincoln Park 2.1 kms from Metro CHICAGO

# 22 out of 50 Vacation Rentals In Chicago

8.9

(31 reviews)

Facilities: Wifi, Pets Allowed, Beach, Garden

Apartment with 13 room options

$131 onwards

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

Michigan Avenue 300 m from Wintrust Arena

# 23 out of 50 Vacation Rentals In Chicago

8.9

(31 reviews)

Facilities: Wifi, Bar, Pets Allowed

$324 onwards

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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

(24 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

8.4

(30 reviews)

Facilities: Wifi, Food, Shuttle Service

Apartment with only 1 room option

$118 onwards

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26. Rustic Mix

Chicago Chinatown 2.0 kms from Douglas Park

# 26 out of 50 Vacation Rentals In Chicago

8.9

(22 reviews)

Facilities: Wifi

Apartment with only 1 room option

$219 onwards

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27. 15 min Ohare/Rivers Casino/Downtown & Parking1

4.5 kms from Northeastern Illinois University

# 27 out of 50 Vacation Rentals In Chicago

7.5

(39 reviews)

Facilities: Wifi, Garden

Apartment with only 1 room option

$131 onwards

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28. Casa Cerca De La Playa

Michigan Avenue 3.3 kms from Stony Island Arts Bank

# 28 out of 50 Vacation Rentals In Chicago

8.6

(24 reviews)

Facilities: Wifi, Bar, Beach, Garden, Food

Apartment with only 1 room option

$232 onwards

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

Michigan Avenue 300 m from Wintrust Arena

# 29 out of 50 Vacation Rentals In Chicago

8.5

(24 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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30. The Neighborhood Hotel Lincoln Park

Lincoln Park 1.1 kms from DePaul University

# 30 out of 50 Vacation Rentals In Chicago

9.1

(19 reviews)

Facilities: Wifi, Food

4 star apartment with 14 room options

$237 onwards

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

Old Town Chicago 600 m from Clark/Division Station

# 31 out of 50 Vacation Rentals In Chicago

8.3

(25 reviews)

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

$279 onwards

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32. Vibrant w/ comforting vibes

Lincoln Park 900 m from Wicker Park

# 32 out of 50 Vacation Rentals In Chicago

8.4

(24 reviews)

Facilities: Wifi

Apartment with only 1 room option

$135 onwards

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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

(18 reviews)

Facilities: Wifi

Apartment with only 1 room option

$271 onwards

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34. Ethan 3 rooms

Chicago Chinatown

# 34 out of 50 Vacation Rentals In Chicago

8.1

(26 reviews)

Facilities: Wifi, Pets Allowed

Apartment with only 1 room option

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35. Luxury chicago suite

Lincoln Park 800 m from North Park University

# 35 out of 50 Vacation Rentals In Chicago

8.3

(24 reviews)

Facilities: Wifi, Bar

$145 onwards

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36. Modern 2 Bedroom in Avondale

Lincoln Park 4.1 kms from North Park University

# 36 out of 50 Vacation Rentals In Chicago

9.1

(18 reviews)

Facilities: Wifi

Apartment with only 1 room option

$217 onwards

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37. Immaculate Brand New Condo Downtown

The Loop 500 m from United Center

# 37 out of 50 Vacation Rentals In Chicago

9.2

(17 reviews)

Facilities: Wifi

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38. Neutral Spiraled Vibes

Chicago Chinatown 2.0 kms from Douglas Park

# 38 out of 50 Vacation Rentals In Chicago

8.9

(18 reviews)

Facilities: Wifi

Apartment with only 1 room option

$179 onwards

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

The Loop 500 m from wndr museum

# 39 out of 50 Vacation Rentals In Chicago

9.1

(16 reviews)

Facilities: Wifi, Pool, Garden

4 star apartment with 6 room options

$396 onwards

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40. McCormick Place spacious 3br-2ba designer suite with optional parking for 8 guests

Michigan Avenue 300 m from Wintrust Arena

# 40 out of 50 Vacation Rentals In Chicago

8.2

(21 reviews)

Hotel McCormick Place is a spacious 3-bedroom designer suite in Chicago that comfortably accommodate (Read More)s up to 8 guests. The hotel offers optional parking and is pet-friendly. The hotel also provides a fitness center, perfect for those wanting to stay active during their stay. Free WiFi is available throughout the property, and all rooms are air-conditioned for a comfortable stay. Famous landmarks such as the McCormick Place Convention Center, Soldier Field, and the Shedd Aquarium are located nearby, making it an ideal choice for both leisure and business travelers.

$653 onwards

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41. Logan Square Modern Apartment

Lincoln Park 4.3 kms from Wicker Park

# 41 out of 50 Vacation Rentals In Chicago

8.8

(17 reviews)

Facilities: Wifi, Pets Allowed, Garden, Food

Apartment with only 1 room option

$215 onwards

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42. Romantic 3 Bed Home In The Heart Of The Park

Michigan Avenue 1.8 kms from University of Chicago

# 42 out of 50 Vacation Rentals In Chicago

7.8

(24 reviews)

Facilities: Wifi, Pets Allowed

$357 onwards

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43. Stunning Condo #2 - Downtown River North

Downtown Chicago 900 m from Clark/Division Station

# 43 out of 50 Vacation Rentals In Chicago

9.1

(15 reviews)

Facilities: Wifi

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44. The Penthouse, Lux stay near Downtown, UofC & Lake

Michigan Avenue 2.9 kms from University of Chicago

# 44 out of 50 Vacation Rentals In Chicago

9.0

(15 reviews)

Facilities: Wifi

$250 onwards

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45. McCormick Place modern and cosy 420 friendly gem on Michigan avenue with optional parking for 6 guests

Michigan Avenue 200 m from Wintrust Arena

# 45 out of 50 Vacation Rentals In Chicago

8.0

(21 reviews)

Reviewers Mention: This McCormick Place gem on Michigan Avenue is a fantastic and gigantic co (Read More)nference space, perfect for events. The location is terrific, with reasonable parking and fast and friendly staff. The trade show had a nice outdoor colonnade and easy transportation options. The Chicago Marathon Expo was a fantastic experience. The restaurant association show had lots of vendors and food. The facility for Nationals was clean but had sparse food options. Overall, the convention center is great, with a car show that showcases awesome cars.

$324 onwards

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