A grand train station with a large glass dome, ornate columns, and a spacious interior.

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chicago Union Station vacation homes

A living room with a dark blue sofa, a dining table with chairs, and a large window with curtains.

1. Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Near North Side
9.4 out of 10, Exceptional, (127 reviews)
"Great space for a large group!"
United States
Sarah M.
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
A beach with palm trees, a white fence, and a city skyline in the background.

2. Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
Downtown Chicago
10.0 out of 10, Exceptional, (24 reviews)
"good place"
United States
Irving Raul Q.
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
A modern living room with a grey sofa, a glass coffee table, and a dining area with a black table and chairs.

3. Heart of the City Group Hub • Patio • Fireplace • Parking

Heart of the City Group Hub • Patio • Fireplace • Parking
Near North Side
9.4 out of 10, Exceptional, (84 reviews)
"This beautiful home is in a great location and safe neighborhood. The metro is nearby and Old Town is there to enjoy. We had a wonderful visit"
United States
Lana S.
Heart of the City Group Hub • Patio • Fireplace • Parking
A spacious living area with a large sectional sofa, a coffee table, and a staircase leading to a kitchen area.

4. Luxury House in the heart of Old Town with Parking

Luxury House in the heart of Old Town with Parking
Near North Side
10.0 out of 10, Exceptional, (67 reviews)
"The house was in a great area, easily walkable to coffee shops and restaurants, and only a short car ride away from downtown. The host was very responsive and accommodating. "
United States
Jessica W.
Luxury House in the heart of Old Town with Parking
A modern building with large windows and a brick facade.

5. Luxury SOHO Styled Two-Level Townhouse - Old Town

Luxury SOHO Styled Two-Level Townhouse - Old Town
Near North Side
10.0 out of 10, Exceptional, (22 reviews)
"Great location in Old Town, walking distance to coffee shops, bars and restaurants. The place is very clean and quiet. I would highly recommend staying here on your next visit to Chicago!"
United States
Brad P.
Luxury SOHO Styled Two-Level Townhouse - Old Town
A row of townhouses with a brick facade, white trim, and multiple windows.

6. Historic luxury townhouse on Chicago's Gold Coast

Historic luxury townhouse on Chicago's Gold Coast
Downtown Chicago
9.6 out of 10, Exceptional, (92 reviews)
"You can’t ask for a better location! We walked to downtown, Millenium Park, and Old Town. The property is gorgeous and a taste of old Chicago with beautiful woodwork and huge bedrooms. The six of us had our own space and were very comfortable."
United States
Angela
Historic luxury townhouse on Chicago's Gold Coast
A modern kitchen with dark cabinetry, a central island with bar stools, a microwave, and a refrigerator.

7. Stylish 3BR Townhouse with 2 Jacuzzi and 1 private garage spot

Stylish 3BR Townhouse with 2 Jacuzzi and 1 private garage spot
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"Was a great place to stay for the weekend!"
United States
Julien J.
Stylish 3BR Townhouse with 2 Jacuzzi and 1 private garage spot
An open doorway with ornate metalwork, leading to a courtyard with a brick building, trees, and outdoor seating.

8. Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.

Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.
Downtown Chicago
10.0 out of 10, Exceptional, (41 reviews)
"Incredible place - pristine, perfect location, all kinds of room to spread out across 4 floors. Would absolutely stay there again "
United States
John B.
Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.
A kitchen with granite countertops, white cabinets, and pendant lighting.

9. Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Near North Side
9.8 out of 10, Exceptional, (119 reviews)
"Excellent location and excellent host"
United States
Jonathan M.
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
A rooftop terrace with a checkered tablecloth, a sofa with colorful cushions, a fire pit, and a city skyline with fireworks in the background.

10. Last-Minute Chicago home with Rooftop Views +Private HOT TUB -Garage-Sleeps 12

Last-Minute Chicago home with Rooftop Views +Private HOT TUB -Garage-Sleeps 12
West Town
10.0 out of 10, Exceptional, (5 reviews)
"Stayed in Chicago for a trade show. Great location and well kept property "
United States
Aaron E.
Last-Minute Chicago home with Rooftop Views +Private HOT TUB -Garage-Sleeps 12
A modern kitchen with wooden cabinets, stainless steel appliances, and a white tiled backsplash.

11. Wabash 4BR - Pool, Free In & Out Parking 1

Wabash 4BR - Pool, Free In & Out Parking 1
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Property is new and really nice. Super clean and well put together. Would stay here again."
United States
Devin D.
Wabash 4BR - Pool, Free In & Out Parking 1
A modern kitchen with a central island, bar stools, stainless steel appliances, and white cabinetry.

12. Brand New 12 Bedroom Mansion

Brand New 12 Bedroom Mansion
Downtown Chicago
The price is AED 5,491
AED 13,061 total
includes taxes & fees
1 Nov - 2 Nov
Brand New 12 Bedroom Mansion
A spacious living area with a fireplace, wooden flooring, and a ceiling with decorative wooden panels.

13. GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)

GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)
Near North Side
9.8 out of 10, Exceptional, (29 reviews)
"This property was perfect for our group of 11 friends. The location was excellent, within walking distance of many attractions, restaurants, and the lake. There was plenty of space for everyone to sleep comfortably, and the host even provided air mattresses, which was a great bonus.I would definitely recommend this property to anyone visiting Chicago. We had a great experience and would gladly stay here again on future trips to the city."
United States
Matthew P.
GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)
A living room with a sofa, armchair, coffee table, and TV stand.

14. Spacious 4-Level/4-Bedroom Townhouse in West Loop

Spacious 4-Level/4-Bedroom Townhouse in West Loop
West Town
10.0 out of 10, Exceptional, (64 reviews)
"We had a very nice experience and everyone was comfortable."
United States
Kirk D.
Spacious 4-Level/4-Bedroom Townhouse in West Loop
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a sink. There are two white bar stools and a wooden dining table with plates and glasses.

15. Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!

Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
South Loop
10.0 out of 10, Exceptional, (13 reviews)
"The location was great and the accommodations were excellent. Great trip"
United States
Cameron O.
Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
A patio with wicker furniture, a hanging chair, and a staircase leading to an upper level.

16. Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly

Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
Near North Side
10.0 out of 10, Exceptional, (6 reviews)
"We enjoyed our stay great host "
United States
Janeth G.
Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
A modern living room with a sofa, a dining table with chairs, a coffee table, and a bookshelf.

17. Pristine Chicago Home - 3BD - 2BA - Free Parking - 2

Pristine Chicago Home - 3BD - 2BA - Free Parking - 2
Downtown Chicago
Pristine Chicago Home - 3BD - 2BA - Free Parking - 2
A spiral staircase with wooden railings and carpeted steps.

18. Gold Coast Home - Rooftop - PoolTable - Parking - Views

Gold Coast Home - Rooftop - PoolTable - Parking - Views
Downtown Chicago
Gold Coast Home - Rooftop - PoolTable - Parking - Views
A laundry room with stacked front-loading washers and dryers, a hallway leading to a living area with a blue chair.

19. Pristine Gold Coast 3BD - 2BA - Free Parking - Beach.

Pristine Gold Coast 3BD - 2BA - Free Parking - Beach.
Downtown Chicago
Pristine Gold Coast 3BD - 2BA - Free Parking - Beach.
Corner building glowing at dusk w/ street views & vibrant urban energy

20. Luxury 4BR 4-Story Chicago Villa |Prime Gold Coast

Luxury 4BR 4-Story Chicago Villa |Prime Gold Coast
Downtown Chicago
Luxury 4BR 4-Story Chicago Villa |Prime Gold Coast
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chicago Union Station Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Good location. Close to lake side parks and museums, close to public transportation and bus. Lake view room can see fireworks in summer from navy pier."
Thomas 2-night trip
Posted 1 hour ago
Congress Plaza Hotel

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