Far Southeast Side Holiday Homes from €187: Search Top House Rentals

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Our top choices for Far Southeast Side holiday homes

A wooden deck with a railing, a staircase, and a window with a wreath.

1. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Robertsdale

Ruth Ann G.

includes taxes & fees

19 Oct - 20 Oct

A bedroom with a stone wall, a TV mounted on it, a bed with a white comforter, and a view of the outdoors through a window.

2. Beautifully furnished one bedroom loft located in Chicago's South side suburb

Hazel Green

Nick L.

includes taxes & fees

18 Oct - 19 Oct

A hot tub with water, a wooden deck, and a chair.

3. Charming 1-bedroom apt in house by creek with AC, in delightful Portage

Portage

Michael T.

A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

4. Romantic Escape - Adult Playhouse with Exotic Dungeon

South Holland

Anonymous traveller

includes taxes & fees

20 Oct - 21 Oct

A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

5. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Westmont

Tomas R.

includes taxes & fees

15 Nov - 16 Nov

Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

6. Theater • Game Room • Gym • Firepit • 4BR Home

Belmont Cragin

Jason

includes taxes & fees

26 Oct - 27 Oct

A cozy outdoor hot tub area with a wooden deck, surrounded by a wooden fence and trees.

7. Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

Miller Beach

Carrah D.

includes taxes & fees

21 Oct - 22 Oct

A living room with a brown sofa, a coffee table, and a patterned rug. There is a staircase leading to another room.

8. Spacious 3br home near Chicago, fenced yard for pets

Richton Park

Greg S.

includes taxes & fees

20 Oct - 21 Oct

A modern living room with a sofa, armchairs, a coffee table, a TV, and a large window with curtains.

9. Spacious 3BR · Bronzeville/South Loop · Sleeps 8

Near South Side

"Excellent stay! The property was clean and an easy walk to McCormick Place convention center. The space was colossal and well appointed, with soap and towels provided for the shower. We were greeted by a wonderful gentleman who took the time to explain the Chicago area to us. Checkout was a breeze—just had to leave our keys—and the instructions were very clear. There was only minimal housekeeping required before leaving the apartment. I would definitely stay here again"

Ilir T.

includes taxes & fees

21 Oct - 22 Oct

A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

10. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Westmont

includes taxes & fees

21 Oct - 22 Oct

11. Arcade • Theater • Gym • Office • Sleeps 15

Portage Park

Daniel J.

includes taxes & fees

24 Oct - 25 Oct

A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

12. Sleeps 18 • 8BR • Game Room • Gym • Theater

Portage Park

Ashley Y.

includes taxes & fees

22 Oct - 23 Oct

A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

13. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Maywood

Carl T.

includes taxes & fees

19 Oct - 20 Oct

A dining area with a black table set for four, surrounded by chairs. A vase with dried flowers and a candle holder are on the table.

14. 3-bedroom house in lovely Matteson with cool AC breeze

Matteson

Susan H.

includes taxes & fees

19 Oct - 20 Oct

A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

15. LUXE 3 BR, 2 BA + Hot Tub

Elmhurst

Anonymous traveller

includes taxes & fees

28 Oct - 29 Oct

A living room with a brick fireplace, a television mounted above it, and a dining area with a table and chairs.

16. Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool

Merrillville

Anonymous traveller

A modern kitchen with wooden cabinets, stainless steel appliances, and a white countertop island.

17. Modern 3BR w/Deck · Minutes from I-65. Fenced Yard

Merrilville

Lynda L.

A cozy living room with a neon sign, a fireplace, a television, and a guitar.

18. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

Lincoln Park

Alison G.

includes taxes & fees

29 Oct - 30 Oct

A modern kitchen with grey cabinets, a central island with stools, a microwave, and a dishwasher.

19. An Escape to a Dream of Green and relaxation.

Miller Beach

Martin R.

includes taxes & fees

18 Oct - 19 Oct

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Top Far Southeast Side Hotel Reviews

Hyatt Regency Chicago

10/10 Excellent

"."

Congress Plaza Hotel

10/10 Excellent

"We stayed at the Congress for a Bears game. We selected it based on price and proximity to Soldier Field. The price was incredibly reasonable, so I was a bit concerned about the quality and cleanliness of the room and hotel prior to checking in. We were more than pleased with our room and the hotel overall and feel it was great value for our money. The room was very clean and had been updated quite recently. It was roomie in both the room itself and the bathroom. We also appreciated the amenities in the room, including a coffee maker, refrigerator, a large, walk-in closet, plenty of drawer storage for clothes and extra seating and table. It is also near do much in the city, so it’s a great place to stay. The only issue that I had is I wish the TV had been a bit larger. But other than that, I would highly recommend the Congress."

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good

"The hotel is in a great location. The room was decent and so was the breakfast. We were entitled to vouchers for breakfast, cocktails and dinner as well as water bottles. At check-in, it would have been nice to be told that and get those vouchers. We had to ask for them the next day after reading a message received from the hotel. It would be nice also at check-in to let us know that housekeeping is every other day. Overall we still had a good stay."

Find out more about Far Southeast Side

Far Southeast Side Holiday Homes information

Number of reviews	310
Accommodation	338 Holiday Homes
Lowest Price	€187
Highest Price	€1,083

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Far Southeast Side holiday homes

1. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

2. Beautifully furnished one bedroom loft located in Chicago's South side suburb

3. Charming 1-bedroom apt in house by creek with AC, in delightful Portage

4. Romantic Escape - Adult Playhouse with Exotic Dungeon

5. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

6. Theater • Game Room • Gym • Firepit • 4BR Home

7. Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

8. Spacious 3br home near Chicago, fenced yard for pets

9. Spacious 3BR · Bronzeville/South Loop · Sleeps 8

10. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

11. Arcade • Theater • Gym • Office • Sleeps 15

12. Sleeps 18 • 8BR • Game Room • Gym • Theater

13. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

14. 3-bedroom house in lovely Matteson with cool AC breeze

15. LUXE 3 BR, 2 BA + Hot Tub

16. Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool

17. Modern 3BR w/Deck · Minutes from I-65. Fenced Yard

18. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

19. An Escape to a Dream of Green and relaxation.

Find holiday rentals that suit your style

Top Far Southeast Side Hotel Reviews

Hyatt Regency Chicago

Congress Plaza Hotel

The Chicago Hotel Collection Ambassador Gold Coast

Fairmont Chicago at Millennium Park

The Godfrey Hotel Chicago

Freehand Chicago

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Find out more about Far Southeast Side

Far Southeast Side Holiday Homes information

Explore a world of travel with Expedia

Holiday Homes in Far Southeast Side

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Far Southeast Side holiday homes

1. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

2. Beautifully furnished one bedroom loft located in Chicago's South side suburb

3. Charming 1-bedroom apt in house by creek with AC, in delightful Portage

4. Romantic Escape - Adult Playhouse with Exotic Dungeon

5. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

6. Theater • Game Room • Gym • Firepit • 4BR Home

7. Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

8. Spacious 3br home near Chicago, fenced yard for pets

9. Spacious 3BR · Bronzeville/South Loop · Sleeps 8

10. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

11. Arcade • Theater • Gym • Office • Sleeps 15

12. Sleeps 18 • 8BR • Game Room • Gym • Theater

13. Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

14. 3-bedroom house in lovely Matteson with cool AC breeze

15. LUXE 3 BR, 2 BA + Hot Tub

16. Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool

17. Modern 3BR w/Deck · Minutes from I-65. Fenced Yard

18. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

19. An Escape to a Dream of Green and relaxation.

Find holiday rentals that suit your style

Top Far Southeast Side Hotel Reviews

Hyatt Regency Chicago

Find out more about Far Southeast Side

Far Southeast Side Holiday Homes information

Explore a world of travel with Expedia