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Zumper

Short Term Rentals in Oakland, IL

25 rentals

1922 W Ogden Ave - Photo 1 of 1

10h ago

9.2

Excellent

Our team has verified this company

Verified

1922 W Ogden Ave

1922 W Ogden Ave, Chicago, IL 60612

Short term | Furnished

1–2 beds

1–2 baths

$2,340–$3,143

Apartment for rent

513 S Damen Ave - Photo 1 of 1

10h ago

9.2

Excellent

Our team has verified this company

Verified

513 S Damen Ave

513 S Damen Ave, Chicago, IL 60612

Short term | Furnished

1 bed

1 bath

$2,619–$3,096

Apartment for rent

1249 W Madison St - Photo 1 of 1

2d ago

Our team has verified this company

Verified

1249 W Madison St, Chicago, IL 60607

Short term | In-unit laundry | Furnished

2 beds

2 baths

$9,562

Apartment for rent

Top amenities
Air Conditioning
Elevator
Garage Parking
In-Unit Laundry
Microwave
Oven
601 West Jackson Boulevard - Photo 1 of 1

2d ago

9.6

Excellent

Our team has verified this company

Verified

601 West Jackson Boulevard

601 W Jackson Blvd #1329, Chicago, IL 60661

Short term | In-unit laundry | Furnished

Studio–2 beds

1–2 baths

$1,860–$5,830

Apartment for rent

Top amenities
Business Center
Central Heat
Concierge Service
Elevator
TV
Wi-Fi
1125 West Van Buren Street - Photo 1 of 1

2d ago

9.6

Excellent

Our team has verified this company

Verified

1125 West Van Buren Street

1125 W Van Buren St, Chicago, IL 60607

Short term | In-unit laundry | Furnished

2–6 beds

2–6 baths

$6,601–$24,767

Apartment for rent

Top amenities
Business Center
Elevator
Furnished
In-Unit Laundry
Oven
Wi-Fi
29 South LaSalle Street - Photo 1 of 1

2d ago

8.4

Very good

Our team has verified this company

Verified

29 South LaSalle Street

29 S La Salle St, Chicago, IL 60603

Short term | In-unit laundry | Furnished

2–8 beds

2–8 baths

$10,424–$29,519

Apartment for rent

Top amenities
Furnished
Microwave
On-Site Management
Swimming Pool
TV
Wi-Fi

Nearby rental good for eco-living

$8,711

Near West Side

Nearby rental good for pet owners

1000 South Michigan Avenue - Photo 1 of 1
3D tour

2d ago

8.4

Very good

Our team has verified this company

Verified

1000 South Michigan Avenue

1000 S Michigan Ave #1286, Chicago, IL 60605

Short term | In-unit laundry | Furnished

Studio–1 bed

1 bath

$2,440–$2,790

Apartment for rent

Top amenities
Air Conditioning
Dishwasher
Furnished
In-Unit Laundry
Oven
Wi-Fi
109 S Paulina St - Photo 1 of 1

2d ago

Our team has verified this company

Verified

109 S Paulina St, Chicago, IL 60612

Short term | In-unit laundry | Furnished

2 beds

1 bath

$8,711

Apartment for rent

Top amenities
Central Heat
Dishwasher
Furnished
In-Unit Laundry
TV
Wi-Fi
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1900 W 17th St - Photo 1 of 1

2d ago

Our team has verified this company

Verified

1900 W 17th St, Chicago, IL 60608

Short term | In-unit laundry | Furnished

2 beds

3 baths

$3,600

$3,314

Price drop

Apartment for rent

Top amenities
Central Heat
Dishwasher
In-Unit Laundry
Microwave
Oven
Wi-Fi
1000 South Clark Street - Photo 1 of 1
3D tour

2d ago

9.6

Excellent

Our team has verified this company

Verified

1000 South Clark Street

1000 S Clark St #1245, Chicago, IL 60605

Short term | In-unit laundry | Furnished

1–2 beds

1–2 baths

$1,840–$4,870

Apartment for rent

Top amenities
Air Conditioning
Assigned Parking
Furnished
In-Unit Laundry
Oven
TV
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Find sweet deals near Oakland

These rentals are 10%-30% cheaper than the local average price for similar rentals.

$1,800

Grand Boulevard

$2,340–$3,143

Near West Side

$1,950

Loop

$2,320

Loop

330 S Wells St #693 - Photo 1 of 1
3D tour

2d ago

Our team has verified this company

Verified

330 S Wells St #693, Chicago, IL 60606

Short term | In-unit laundry | Furnished

1 bed

1 bath

$2,550

$2,320

Price drop

Apartment for rent

Top amenities
Dishwasher
Furnished
Microwave
Roof Deck
Storage
Wi-Fi
730 S Clark St #1280 - Photo 1 of 1
3D tour

3d ago

Our team has verified this company

Verified

730 S Clark St #1280, Chicago, IL 60605

Short term | In-unit laundry | Furnished

1 bed

1 bath

$2,860

$1,950

Price drop

Apartment for rent

Top amenities
Central Heat
Concierge Service
Furnished
In-Unit Laundry
Microwave
Residents Lounge
901 S Ashland Ave #1385 - Photo 1 of 1
3D tour

4d ago

Our team has verified this company

Verified

901 S Ashland Ave #1385, Chicago, IL 60607

Short term | Furnished | Air conditioning

1 bed

1 bath

$2,360

$1,510

Price drop

Apartment for rent

Top amenities
Air Conditioning
Business Center
Microwave
On-Site Laundry
Oven
TV
1220 W Jackson Blvd #1320 - Photo 1 of 1
3D tour

4d ago

Our team has verified this company

Verified

1220 W Jackson Blvd #1320, Chicago, IL 60607

Short term | In-unit laundry | Furnished

1 bed

1 bath

$2,210

$1,810

Price drop

Apartment for rent

Top amenities
Business Center
Elevator
Furnished
In-Unit Laundry
Roof Deck
Wi-Fi
812 W Adams St #1254 - Photo 1 of 1
3D tour

5d+ ago

Our team has verified this company

Verified

812 W Adams St #1254, Chicago, IL 60607

Short term | In-unit laundry | Furnished

1 bed

1 bath

$2,960

$2,690

Price drop

Apartment for rent

Top amenities
Dishwasher
Elevator
Furnished
In-Unit Laundry
Microwave
Wi-Fi
5323 S Harper Ave - Photo 1 of 1

5d+ ago

Short Term Hyde Park house for rent in Chicago

5323 S Harper Ave, Chicago, IL 60615

Short term | In-unit laundry | Hardwood floor

2 beds

2 baths

$2,300

House for rent

Top amenities
In-Unit Laundry
214 W 31st St ##1e - Photo 1 of 1

5d+ ago

Short Term Armour Square condo for rent in Chicago

214 W 31st St ##1e, Chicago, IL 60616

Short term | Air conditioning | On-site laundry

2 beds

2 baths

$2,300

Condo for rent

Top amenities
Air Conditioning
On-Site Laundry
445 W 37th St - Photo 1 of 1

5d+ ago

Short Term Bridgeport apartment for rent in Chicago

445 W 37th St, Chicago, IL 60609

Short term | Air conditioning

Studio

1 bath

$1,950

Apartment for rent

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2821 S Emerald Ave ##1r - Photo 1 of 1

5d+ ago

Short Term Bridgeport apartment for rent in Chicago

2821 S Emerald Ave ##1r, Chicago, IL 60616

Short term | Garage parking | Assigned parking

2 beds

1 bath

$1,900

Apartment for rent

445 W 37th St ##1 - Photo 1 of 1

5d+ ago

Short Term Bridgeport apartment for rent in Chicago

445 W 37th St ##1, Chicago, IL 60609

Short term | Air conditioning

3 beds

1 bath

$2,200

Apartment for rent

31 E 26th St - Photo 1 of 1

5d+ ago

Short Term Douglas condo for rent in Chicago

31 E 26th St, Chicago, IL 60616

Short term | In-unit laundry | Garage parking

2 beds

2 baths

$2,600

Condo for rent

Top amenities
Assigned Parking
Garage Parking
In-Unit Laundry
2821 S Emerald Ave ##2r - Photo 1 of 1

5d+ ago

Short Term Bridgeport condo for rent in Chicago

2821 S Emerald Ave ##2r, Chicago, IL 60616

Short term | Garage parking | Assigned parking

2 beds

1 bath

$1,900

Condo for rent

3013 S Wells St ##2 - Photo 1 of 1

5d+ ago

Short Term Armour Square condo for rent in Chicago

3013 S Wells St ##2, Chicago, IL 60616

Short term | Garage parking | On-site laundry

3 beds

1 bath

$1,975

Condo for rent

Top amenities
On-Site Laundry
50 E 26th St - Photo 1 of 1

5d+ ago

Short Term South Loop house for rent in Chicago

50 E 26th St, Chicago, IL 60616

Short term | On-site laundry | Balcony

2 beds

2 baths

$3,100

House for rent

Top amenities
On-Site Laundry
4600 S Indiana Ave - Photo 1 of 1

5d+ ago

Short Term Grand Boulevard house for rent in Chicago

4600 S Indiana Ave, Chicago, IL 60653

Short term | In-unit laundry | Fireplace

3 beds

2 baths

$1,800

House for rent

Top amenities
In-Unit Laundry
Showing 1 - 25 of 25 results
Home > Apartments in Chicago > Oakland > Oakland Short term rentals
Updated: March 15, 2026

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Looking for short term apartments in Oakland, Chicago, IL near you?

🔑Available apartment rentals25
💰Best rent deal901 S Ashland Ave #1385
✨Popular amenities, ,

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