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Short Term Rentals in Oakland, IL

25 rentals

2018 W 21st Pl - Photo 1 of 1

18h ago

Our team has verified this company

Verified

2018 W 21st Pl, Chicago, IL 60608

Short term | In-unit laundry | Furnished

4 beds

3 baths

$9,000

Apartment for rent

Top amenities
Air Conditioning
Central Heat
Dishwasher
In-Unit Laundry
Microwave
TV
755 S Clark St - Photo 1 of 1

18h ago

Our team has verified this company

Verified

755 S Clark St, Chicago, IL 60605

Short term | In-unit laundry | Furnished

1 bed

1 bath

$8,390

Apartment for rent

Top amenities
Dishwasher
In-Unit Laundry
Oven
Swimming Pool
TV
Wi-Fi
1243 W Madison St - Photo 1 of 1

18h ago

Our team has verified this company

Verified

1243 W Madison St, Chicago, IL 60607

Short term | In-unit laundry | Furnished

2 beds

2 baths

$6,965

Apartment for rent

Top amenities
Central Heat
Dishwasher
Furnished
Oven
TV
Wi-Fi
4241 S Langley Ave - Photo 1 of 1

18h ago

Our team has verified this company

Verified

4241 S Langley Ave, Chicago, IL 60653

Short term | In-unit laundry | Furnished

3 beds

1 bath

$5,250

Apartment for rent

Top amenities
Business Center
Dishwasher
Furnished
In-Unit Laundry
TV
Wi-Fi
2207 W 18th St - Photo 1 of 1

18h ago

Our team has verified this company

Verified

2207 W 18th St, Chicago, IL 60608

Short term | In-unit laundry | Furnished

2 beds

2 baths

$2,866

Apartment for rent

Top amenities
Air Conditioning
Central Heat
Dishwasher
In-Unit Laundry
Oven
TV
1044 West Van Buren Street - Photo 1 of 1

18h ago

9.6

Excellent

Our team has verified this company

Verified

1044 West Van Buren Street

1044 W Van Buren St, Chicago, IL 60607

Short term | In-unit laundry | Furnished

6 beds

6 baths

$21,182

Price drop

Apartment for rent

Top amenities
Air Conditioning
Central Heat
Dishwasher
Microwave
Oven
Wi-Fi

Nearby rental good for eco-living

$6,965

Near West Side

Nearby rental good for pet owners

1125 West Van Buren Street - Photo 1 of 1

18h 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

6 beds

6 baths

$15,734

Price drop

Apartment for rent

Top amenities
Air Conditioning
In-Unit Laundry
Microwave
Oven
TV
Wi-Fi
1220 W Jackson Blvd #1320 - Photo 1 of 1
3D tour

18h 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

$2,590

$2,120

Price drop

Apartment for rent

Top amenities
Business Center
Elevator
Furnished
In-Unit Laundry
Roof Deck
Wi-Fi
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601 West Jackson Boulevard - Photo 1 of 1

19h ago

9.6

Excellent

Our team has verified this company

Verified

601 West Jackson Boulevard

601 W Jackson Blvd #1307, Chicago, IL 60661

Short term | In-unit laundry | Furnished

Studio–2 beds

1–2 baths

$1,860–$3,430

Apartment for rent

Top amenities
Business Center
Central Heat
Dishwasher
Roof Deck
TV
Wi-Fi
801 S Western Ave - Photo 1 of 1

19h ago

Our team has verified this company

Verified

801 S Western Ave, Chicago, IL 60612

Short term | In-unit laundry | Furnished

2 beds

2 baths

$3,838

Apartment for rent

Top amenities
Central Heat
In-Unit Laundry
Microwave
Oven
TV
Wi-Fi
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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

$2,318–$3,164

Near West Side

$2,120

Near West Side

$2,100

Near West Side

1000 South Michigan Avenue - Photo 1 of 1

19h ago

9

Excellent

Our team has verified this company

Verified

1000 South Michigan Avenue

1000 S Michigan Ave, Chicago, IL 60605

Short term | In-unit laundry | Furnished

Studio–6 beds

1–6 baths

$2,600–$27,201

Apartment for rent

Top amenities
Air Conditioning
Assigned Parking
Elevator
On-Site Management
Swimming Pool
TV
1909 S Michigan Ave - Photo 1 of 1

19h ago

Our team has verified this company

Verified

1909 S Michigan Ave, Chicago, IL 60616

Short term | In-unit laundry | Furnished

3 beds

2 baths

$17,282

$13,974

Price drop

Apartment for rent

Top amenities
Assigned Parking
Dishwasher
Elevator
Fireplace
In-Unit Laundry
Oven
1411 S Michigan Ave - Photo 1 of 1

19h ago

Our team has verified this company

Verified

1411 S Michigan Ave, Chicago, IL 60605

Short term | In-unit laundry | Furnished

3 beds

3 baths

$8,970

Apartment for rent

Top amenities
Air Conditioning
Dishwasher
In-Unit Laundry
Package Service
TV
Wi-Fi
829 S Wabash Ave - Photo 1 of 1

19h ago

Our team has verified this company

Verified

829 S Wabash Ave, Chicago, IL 60605

Short term | Furnished | Air conditioning

2 beds

1 bath

$9,972

$6,200

Price drop

Apartment for rent

Top amenities
Air Conditioning
Elevator
Furnished
Microwave
Oven
Wi-Fi
3715 S Giles Ave - Photo 1 of 1

19h ago

Our team has verified this company

Verified

3715 S Giles Ave, Chicago, IL 60653

Short term | Furnished | Air conditioning

3 beds

2 baths

$2,614

$2,284

Price drop

Apartment for rent

Top amenities
Business Center
Dishwasher
Furnished
Microwave
On-Site Laundry
TV
812 W Adams St #1256 - Photo 1 of 1
3D tour

19h ago

Our team has verified this company

Verified

812 W Adams St #1256, Chicago, IL 60607

Short term | Furnished | Air conditioning

1 bed

1 bath

$2,620

$2,100

Price drop

Apartment for rent

Top amenities
Air Conditioning
Central Heat
Furnished
Microwave
Oven
TV
5252 South Cornell Avenue - Photo 1 of 1

19h ago

8.4

Very good

Our team has verified this company

Verified

5252 South Cornell Avenue

5252 S Cornell Ave #1158, Chicago, IL 60615

Short term | In-unit laundry | Furnished

1–2 beds

1–2 baths

$2,250–$4,280

Price drop

Apartment for rent

Top amenities
Air Conditioning
Furnished
In-Unit Laundry
Microwave
Oven
TV
834 W Monroe St #773 - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

834 W Monroe St #773, Chicago, IL 60607

Short term | In-unit laundry | Furnished

Studio

1 bath

$2,750

Apartment for rent

Top amenities
Dishwasher
Furnished
In-Unit Laundry
Roof Deck
TV
Wi-Fi
Advertisement
1922 W Ogden Ave - Photo 1 of 1
Rent special

5d+ 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

$2,318–$3,164

Apartment for rent

513 S Damen Ave - Photo 1 of 1

5d+ 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

$2,629–$3,149

Apartment for rent

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

730 S Clark St #1280 - Photo 1 of 1

5d+ 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

$2,850

Apartment for rent

Top amenities
Central Heat
Concierge Service
Elevator
Furnished
In-Unit Laundry
Microwave
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: January 29, 2026

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

🔑Available apartment rentals25
💰Best rent deal4600 S Indiana Ave
✨Popular amenities, ,

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