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Short Term Rentals in Oakland, IL

25 rentals

417 S Dearborn St - Photo 1 of 1

1h ago

Our team has verified this company

Verified

417 S Dearborn St, Chicago, IL 60605

Short term | In-unit laundry | Furnished

2 beds

1 bath

$8,247

Apartment for rent

Top amenities
Central Heat
Elevator
Furnished
In-Unit Laundry
Residents Lounge
TV
1243 West Madison Street - Photo 1 of 1

1h ago

8.4

Very good

Our team has verified this company

Verified

1243 West Madison Street

1243 W Madison St, Chicago, IL 60607

Short term | In-unit laundry | Furnished

2–3 beds

2 baths

$9,489–$9,711

Apartment for rent

Top amenities
Elevator
Furnished
Garage Parking
In-Unit Laundry
Oven
TV
1125 West Van Buren Street - Photo 1 of 1

1h ago

8.4

Very good

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

4–6 beds

4–6 baths

$20,447–$28,808

Apartment for rent

Top amenities
Air Conditioning
Central Heat
Dishwasher
In-Unit Laundry
Oven
Wi-Fi
1000 South Michigan Avenue - Photo 1 of 1

1h ago

8.4

Very good

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–2 beds

1–2 baths

$2,890–$18,343

Apartment for rent

Top amenities
Air Conditioning
Assigned Parking
Elevator
On-Site Management
Swimming Pool
TV
109 S Paulina St - Photo 1 of 1

1h 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

$9,646

Apartment for rent

Top amenities
Central Heat
Dishwasher
Furnished
In-Unit Laundry
TV
Wi-Fi
633 South LaSalle Street - Photo 1 of 1

1h ago

8.4

Very good

Our team has verified this company

Verified

633 South LaSalle Street

633 S La Salle St, Chicago, IL 60605

Short term | In-unit laundry | Furnished

3 beds

3 baths

$15,535

Apartment for rent

Top amenities
Air Conditioning
Elevator
Furnished
Swimming Pool
TV
Wi-Fi

Nearby rental good for eco-living

$12,516

South Loop

Nearby rental good for pet owners

226 South Hoyne Avenue - Photo 1 of 1

1h ago

9

Excellent

Our team has verified this company

Verified

226 South Hoyne Avenue

226 S Hoyne Ave, Chicago, IL 60612

Short term | In-unit laundry | Furnished

6 beds

4 baths

$15,016

Apartment for rent

Top amenities
Furnished
In-Unit Laundry
Microwave
Oven
TV
Wi-Fi
1909 S Michigan Ave - Photo 1 of 1

1h 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

$13,914

$12,516

Price drop

Apartment for rent

Top amenities
Assigned Parking
Dishwasher
Elevator
Fireplace
In-Unit Laundry
Oven
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1212 South Michigan Avenue - Photo 1 of 1

1h ago

9.6

Excellent

Our team has verified this company

Verified

1212 South Michigan Avenue

1212 S Michigan Ave #1080, Chicago, IL 60605

Short term | Furnished | Air conditioning

1–2 beds

1–2 baths

$2,750–$4,250

Apartment for rent

Top amenities
Furnished
Microwave
On-Site Laundry
Roof Deck
TV
Wi-Fi
1210 South Indiana Avenue - Photo 1 of 1

1h ago

9.6

Excellent

Our team has verified this company

Verified

1210 South Indiana Avenue

1210 S Indiana Ave #1043, Chicago, IL 60605

Short term | In-unit laundry | Furnished

Studio–3 beds

1–2 baths

$2,750–$6,620

Apartment for rent

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

Find sweet deals near Oakland

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

$1,800

Grand Boulevard

$2,360

Loop

$2,420–$3,660

Loop

$1,600

Lower West Side

903 South Ashland Avenue - Photo 1 of 1
3D tour

1h ago

9.6

Excellent

Our team has verified this company

Verified

903 South Ashland Avenue

903 S Ashland Ave #720, Chicago, IL 60607

Short term | Furnished | Air conditioning

1 bed

1 bath

$3,490

Apartment for rent

Top amenities
Assigned Parking
Dishwasher
Microwave
On-Site Laundry
TV
Wi-Fi
5252 South Cornell Avenue - Photo 1 of 1

3h ago

9

Excellent

Our team has verified this company

Verified

5252 South Cornell Avenue

5252 S Cornell Ave #1157, Chicago, IL 60615

Short term | In-unit laundry | Furnished

1–2 beds

1–2 baths

$2,430–$3,650

Apartment for rent

Top amenities
Central Heat
Elevator
In-Unit Laundry
Oven
Swimming Pool
TV
513 S Damen Ave - Photo 1 of 1

1d 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

$2,816–$3,290

Apartment for rent

1035 West Van Buren Street - Photo 1 of 1

1d ago

9.6

Excellent

Our team has verified this company

Verified

1035 West Van Buren Street

1035 W Van Buren St #1164, Chicago, IL 60607

Short term | In-unit laundry | Furnished

Studio–2 beds

1 bath

$2,580–$4,630

Apartment for rent

Top amenities
Air Conditioning
Central Heat
In-Unit Laundry
Microwave
Swimming Pool
Wi-Fi
601 West Jackson Boulevard - Photo 1 of 1

1d 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

$2,550–$5,820

Apartment for rent

Top amenities
Business Center
Concierge Service
EV Charging
Swimming Pool
TV
Wi-Fi
1407 South Michigan Avenue - Photo 1 of 1

1d ago

9.6

Excellent

Our team has verified this company

Verified

1407 South Michigan Avenue

1407 S Michigan Ave #856, Chicago, IL 60605

Short term | In-unit laundry | Furnished

Studio–1 bed

1 bath

$2,360–$4,190

Apartment for rent

Top amenities
Central Heat
Concierge Service
Dishwasher
In-Unit Laundry
Oven
Swimming Pool
1922 W Ogden Ave - Photo 1 of 1

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

$2,541–$3,304

Apartment for rent

1220 W Jackson Blvd #1320 - Photo 1 of 1

5d+ 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

$2,980

Apartment for rent

Top amenities
Business Center
Elevator
Furnished
In-Unit Laundry
Roof Deck
Wi-Fi
Advertisement
730 S Clark St #1327 - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

730 S Clark St #1327, Chicago, IL 60605

Short term | In-unit laundry | Furnished

1 bed

1 bath

$2,940

Apartment for rent

Top amenities
Dishwasher
Elevator
Furnished
In-Unit Laundry
Microwave
TV
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

$1,900

Apartment for rent

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

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: May 1, 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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