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22 Aug - 23 Aug
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23 Aug - 24 Aug
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28 Aug - 30 Aug
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4 Sep - 6 Sep

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Our top choices for Oak Street hotels

1. The Sono Chicago

The Sono Chicago
Old Town Chicago, 1.5 km from Oak Street
United States
Bronwyn
AED 562
AED 660 total
includes taxes & fees
1 Sep - 2 Sep
The Sono Chicago

2. The Langham, Chicago

The Langham, Chicago
River North, 1.4 km from Oak Street
United States
Christopher
AED 2,068
AED 2,459 total
includes taxes & fees
7 Sep - 8 Sep
The Langham, Chicago

3. The Peninsula Chicago

The Peninsula Chicago
Streeterville, 0.5 km from Oak Street
United States
Justin
AED 2,296
AED 2,729 total
includes taxes & fees
23 Aug - 24 Aug
The Peninsula Chicago

4. Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago
River North, 1.3 km from Oak Street
United States
Jorge
AED 1,722
AED 2,047 total
includes taxes & fees
30 Aug - 31 Aug
Trump International Hotel & Tower Chicago

5. L7 Chicago by LOTTE

L7 Chicago by LOTTE
Theatre District, 1.6 km from Oak Street
United States
Girivasan
AED 790
AED 939 total
includes taxes & fees
30 Aug - 31 Aug
L7 Chicago by LOTTE

6. Park Hyatt Chicago

Park Hyatt Chicago
Streeterville, 0.4 km from Oak Street
United States
Jennifer
AED 2,033
AED 2,417 total
includes taxes & fees
30 Aug - 31 Aug
Park Hyatt Chicago

7. The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Streeterville, 1 km from Oak Street
United States
Jennifer
AED 1,392
AED 1,764 total
includes taxes & fees
23 Aug - 24 Aug
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

8. Nobu Hotel Chicago

Nobu Hotel Chicago
2.6 km from Oak Street
Canada
Jordan
AED 1,511
AED 1,888 total
includes taxes & fees
30 Aug - 31 Aug
Nobu Hotel Chicago

9. Moxy Chicago Downtown

Moxy Chicago Downtown
River North, 1.1 km from Oak Street
United States
Julia
AED 661
AED 786 total
includes taxes & fees
7 Sep - 8 Sep
Moxy Chicago Downtown

10. The LaSalle Chicago, Autograph Collection by Marriott

The LaSalle Chicago, Autograph Collection by Marriott
Theatre District, 2.5 km from Oak Street
United States
Anthony
AED 1,186
AED 1,411 total
includes taxes & fees
6 Sep - 7 Sep
The LaSalle Chicago, Autograph Collection by Marriott

11. Aloft by Marriott Chicago Downtown River North

Aloft by Marriott Chicago Downtown River North
River North, 1.1 km from Oak Street
United States
Ronald
AED 624
AED 742 total
includes taxes & fees
7 Sep - 8 Sep
Aloft by Marriott Chicago Downtown River North

12. Waldorf Astoria Chicago

Waldorf Astoria Chicago
0.2 km from Oak Street
United States
Jim
AED 1,951
AED 2,320 total
includes taxes & fees
30 Aug - 31 Aug
Waldorf Astoria Chicago

13. citizenM Chicago Downtown

citizenM Chicago Downtown
Theatre District, 1.5 km from Oak Street
United States
lakadria
AED 624
AED 742 total
includes taxes & fees
7 Sep - 8 Sep
citizenM Chicago Downtown

14. Canopy by Hilton Chicago Central Loop

Canopy by Hilton Chicago Central Loop
The Loop, 2.6 km from Oak Street
United States
Nichol
AED 840
AED 998 total
includes taxes & fees
30 Aug - 31 Aug
Canopy by Hilton Chicago Central Loop

15. Four Seasons Hotel Chicago

Four Seasons Hotel Chicago
Streeterville, 0.2 km from Oak Street
United States
August
AED 1,983
AED 2,358 total
includes taxes & fees
30 Aug - 31 Aug
Four Seasons Hotel Chicago

16. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
The Loop, 1.4 km from Oak Street
United States
Luis
AED 777
AED 1,032 total
includes taxes & fees
7 Sep - 8 Sep
LondonHouse Chicago, Curio Collection by Hilton

17. Residence Inn Chicago Downtown/Loop

Residence Inn Chicago Downtown/Loop
Theatre District, 2.2 km from Oak Street
Canada
Renato
AED 871
AED 1,035 total
includes taxes & fees
30 Aug - 31 Aug
Residence Inn Chicago Downtown/Loop

18. The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown
The Loop, 1.5 km from Oak Street
United States
Brandon
AED 713
AED 965 total
includes taxes & fees
1 Sep - 2 Sep
The Royal Sonesta Chicago Downtown

19. Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop
The Loop, 2.6 km from Oak Street
United States
Theresa
AED 618
AED 735 total
includes taxes & fees
7 Sep - 8 Sep
Hilton Garden Inn Chicago Central Loop

20. Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
Theatre District, 2.1 km from Oak Street
United States
Xiao
AED 531
AED 743 total
includes taxes & fees
30 Aug - 31 Aug
Silversmith Hotel Chicago Downtown
View all properties

Compare popular hotels close to Oak Street

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
Private kitchen
The Sono Chicago
10.0
Exceptional
541 reviews
View
Lobby
The Langham, Chicago
9.8
Exceptional
1,014 reviews
View
Front of property - evening/night
The Peninsula Chicago
9.8
Exceptional
1,008 reviews
View
Terrace/patio
Trump International Hotel & Tower Chicago
9.6
Exceptional
1,997 reviews
View
Breakfast, lunch, dinner and brunch served
Park Hyatt Chicago
9.6
Exceptional
1,001 reviews
View

Top Oak Street Hotel Reviews

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

8/10 Good
"They charge a facilities fee which is about 20 bucks a night for the amenities. I generally don't have a problem with that as it includes breakfast. BUT, I was annoyed that in the hotel gym (which isn't bad), the bikes had some problems. It's a slight nitpick, admittedly, but that's what it is. The hotel is very close to transit and the LOOP which is the main area of Chicago. Staff were amazing and helpful, the breakfast was very filling. The gym has weights that go up to 20KG, which is pretty nice and they do have those gymbro slogans on the walls which is kind of fun."
Justin 4-night trip
Posted 6 hours ago
Hotel Riu Plaza Chicago
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Very nice staff. Terrific location. Comfortable room"
Charles 1-night trip
Posted 7 hours ago
InterContinental Chicago Magnificent Mile by IHG
Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Very nice hotel. We had a King size bed overlooking Buckingham fountain. Booking a park view room is highly recommended. The shower/bathroom is on the smaller end, however, knowing the history of the hotel, it comes at no surprise. The hotel itself has so much history and has quite a few famous guests throughout it's time. We are already planning our next trip back to Chicago and will likely stay here again! Highly recommend staying here!"
Alexandra 1-night trip
Posted 11 hours ago
Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

8/10 Good
"I arrived well after check-in and the room was not ready. Was ready late."
Luis Eduardo 2-night trip
Posted 11 hours ago
Hilton Chicago/Magnificent Mile Suites
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

8/10 Good
"The location could not be better--close to Michigan Avenue and the Red Line L--and the property is clean, quiet, and safe. The only thing that rankled were the elevators, for which one typically has to wait years for: ended up taking the stairs often, and I was staying on the 9th floor."
Andrew 2-night trip
Posted 14 hours ago
Hotel Saint Clair- Magnificent Mile
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

8/10 Good
"There are two elevators in the lobby. One was out of service, which seems to be a common occurrence there. It made the wait to get to or from your room difficult."
Donald 3-night trip
Posted 17 hours ago
Thompson Chicago, by Hyatt
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

10/10 Excellent
"Awesome stay. I love the property. Staff comfort me when I found out that my dad passed away. This is/was going beyond the call of duty and doing an extra great job so 10 stars. You are greatly appreciated. Primetime location downtown near magnificent mile and Navy Pier,"
George 5-night trip
Posted 20 hours ago
Kasa Magnificent Mile Chicago
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

10/10 Excellent
"Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around"
Vivek 2-night trip
Posted 6 days ago
Four Seasons Hotel Chicago

Other attractions near Oak Street

A large indoor Christmas tree in a shopping mall.
Photo by Rita Irvine

900 North Michigan Shops

8.6/10 (55 reviews)
You can browse for the perfect souvenirs at 900 North Michigan Shops during your visit to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.
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A tall skyscraper with a spire, a flagpole with an American flag, and a stone building with arched windows.

875 North Michigan Avenue

9.2/10 (2,926 reviews)
You can find out about the history of Chicago with a visit to 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its fascinating museums.
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Topgolf Swing Suite

You can take time to visit Topgolf Swing Suite during your travels to Chicago. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
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Mariano Plaza

After visiting Mariano Plaza, make a plan to see the other sights and activities in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.
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The Drake

The Drake is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the entertainment choices in this vibrant area.
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Fourth Presbyterian Church

10.0/10 (2 reviews)
Fourth Presbyterian Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed art scene.
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360 CHICAGO

You can learn about the history of Chicago with a visit to 360 CHICAGO. Amble around this vibrant area's riverfront or experience its fascinating museums.
See properties

Bronzeville Black Chamber of Commerce

Find out about the history of Chicago with a stop at Bronzeville Black Chamber of Commerce. Discover the entertainment choices and notable monuments in this vibrant area.
See properties

Find out more about Oak Street

Top reasons to visit Oak Street

  • Upscale Shopping: Oak Street is renowned for its luxury boutiques and designer stores, offering a premier shopping experience.
  • Beautiful Oak Street Beach: Enjoy relaxation and recreational activities at the stunning beach along Lake Michigan.
  • Cultural Enrichment: Explore nearby art museums and urban parks that showcase Chicago's rich culture and vibrant atmosphere.
  • Wildlife Encounters: Experience opportunities to connect with local wildlife in the surrounding parks and natural areas.
  • Diverse Accommodations: Choose from a variety of lodging options, including pet-friendly hotels and cozy apartments.

Find great hotels near Oak Street

Discover a variety of accommodation options along Oak Street, Chicago, designed to meet your every need. Whether you're seeking a pet-friendly hotel, a cozy apartment, or a business-friendly stay, the area offers diverse choices. With convenient access to Oak Street Beach and vibrant shopping experiences, you'll find the perfect place to relax and unwind during your visit to this iconic city.

  • Hyatt Regency Chicago: This 4-star hotel offers a vibrant city-themed experience located in the heart of the shopping district, only 1.4km from Oak Street. Ideal for travelers seeking a blend of urban excitement and nature, the Hyatt Regency Chicago features spacious rooms with stunning city views. Guests can indulge in various amenities, including a fitness center, on-site dining options, and access to nearby shopping venues. Its central location makes it perfect for those looking to explore the city while enjoying modern comforts.
  • The Whitehall Hotel, BW Premier Collection: Situated a mere 161m from Oak Street, this charming 4-star boutique hotel is perfect for pet-friendly travelers and business visitors alike. The Whitehall Hotel boasts uniquely designed rooms adorned with distinctive decor and artworks, creating a cozy yet sophisticated atmosphere. With a pet-friendly policy allowing pets onsite, guests can enjoy their stay worry-free. Additional amenities include business services and a welcoming ambiance, making it a great choice for those looking for a home away from home in the city.
  • LondonHouse Chicago, Curio Collection by Hilton: This luxurious 4.5-star hotel is located 1.4km from Oak Street and offers an exceptional spa-themed experience. LondonHouse Chicago welcomes LGBTQIA travelers and features a full-service spa with various relaxation options, including massages and hydrotherapy treatments. The hotel's rooftop bar provides breathtaking views of the city skyline, perfect for unwinding after a day of shopping in the nearby district. With modern design and a commitment to inclusivity, this hotel is a standout choice for discerning visitors.

Where to stay near Oak Street

Oak Street offers a delightful blend of experiences, from romantic strolls along its scenic beach to family-friendly parks nearby. Explore upscale shopping along the iconic Oak Street boutiques and enjoy the vibrant atmosphere of the surrounding neighborhoods. With picturesque locations and friendly locals, you'll find both relaxation and adventure just steps away from the beach, making it the perfect destination for any traveler seeking a unique urban experience.

  • Chicago: As a vibrant metropolis, Chicago is the heart of the Midwest, with Oak Street nestled within its bustling core. Known for its rich cultural scene, Chicago attracts travelers year-round, with peak visitor numbers from June to August. This city offers an ideal blend of family-friendly attractions, outdoor activities, and urban experiences. Don't miss the chance to explore its famous shopping districts, iconic theaters, and state-of-the-art sports facilities, all within easy reach. The local landmarks, including Millennium Park and Navy Pier, make Chicago a must-visit destination for any traveler.
  • Downtown Chicago: Situated in the very center of the city, Downtown Chicago is a lively neighborhood that encompasses Oak Street. With consistent visitor numbers throughout the year, it also sees peaks during the summer months. Families and outdoor enthusiasts flock to this area for its array of attractions, including renowned shopping spots, entertainment arenas, and theaters. Notable landmarks such as Grant Park and the Art Institute of Chicago are just a stone's throw away, providing ample opportunities for exploration and enjoyment in this vibrant urban landscape.
  • Magnificent Mile: Located a mere 644m from Oak Street, the Magnificent Mile is renowned for its upscale shopping and vibrant atmosphere. This neighborhood draws visitors year-round, particularly during the spring and summer seasons. Travelers come here for family activities and urban adventures, with easy access to shopping areas, educational venues, and entertainment facilities. Highlights include the iconic John Hancock Center and the scenic waterfront at the jetty pier, making the Magnificent Mile a perfect blend of leisure and excitement for any visitor.

Things to do near Oak Street

When visiting Oak Street in Chicago, you'll find a vibrant mix of activities, including shopping at upscale boutiques and exploring nearby city attractions. Don't miss the chance to enjoy water sports along the shores of Lake Michigan, where you can engage in various recreational activities. Additionally, the area offers opportunities for wildlife encounters, making it a well-rounded destination for any tourist.

Shopping

On Oak Street, you can explore the 900 North Michigan Shops, just 161m away, offering a vibrant mix of entertainment and family-friendly vibes. Also nearby is the Chicago Place Mall, 644m away, perfect for a family outing. Don’t miss the Harry Potter Shop Chicago, also 644m away, for some magical souvenirs.

Recreation

At Wrigley Field, immerse yourself in the energetic atmosphere of a live baseball game, just 6.4km from Oak Street. Enjoy soulful music at the House of Blues Chicago, only 1.4km away. For tranquility, visit Northerly Island Natural Area, a serene escape 4.8km from Oak Street.

Adventure

Embark on an adventure at Salt Creek Trail, a scenic hiking destination located 19.3km from Oak Street, offering beautiful outdoor vibes. For a splash of fun, visit Rainbow Falls Waterpark, situated 32.2km away, where you can enjoy thrilling water slides and family-friendly entertainment.

Nightlife

Experience the vibrant nightlife on Oak Street with a visit to the Chicago Theatre, offering romance and culture just 1.6km away. For a fun pub atmosphere, check out Dave & Buster's, only 483m away, or embark on an adventure at Amazing Chicago's Funhouse Maze, also 1.6km away.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Oak Street

To save money during your visit to Oak Street, consider traveling in the off-peak months of December to February, when hotel prices are lower. Aim to book your stay on a Monday, as it’s the least expensive day. Utilize Expedia's search tools to find eco-friendly hotels and sort results by price for the best deals. Additionally, combine your hotel stay with flights and activities to secure package discounts. For budget-friendly transportation, explore public transit options, and take advantage of free local attractions to enhance your experience without overspending.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Oak Street are December to February, where the prices are slightly lower. This is in comparison to June and September to October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Oak Street is Monday. The most expensive day to stay around Oak Street is Saturday.
  • Find cheap hotels on Expedia: Certainly. Here's a paraphrased version of your text in a trusted and attentive tone:Utilize Expedia’s search tool to customize your options based on your budget, desired location, and preferred hotel type. For instance, selecting the “Eco-certified” filter will showcase sustainable and environmentally friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay on Oak Street with your flights and activities through an Expedia package deal.

Find the best attractions near Oak Street

Oak Street, Chicago offers a vibrant experience with its iconic skyscrapers, lush urban parks, and captivating art museums. This area is perfect for those seeking cultural enrichment and family-friendly activities. Don't miss the beautiful Oak Street Beach, ideal for relaxation and recreation. For convenience, consider staying at nearby motels to fully enjoy your visit to this lively neighborhood.

  • Michigan Avenue: Experience the vibrant energy of Michigan Avenue, also known as the Magnificent Mile. This bustling street features a mix of high-end shopping, dining, and iconic architecture, making it a must-visit for those looking to immerse themselves in the city's urban vibe.
  • Navy Pier: Enjoy the scenic views and friendly atmosphere at Navy Pier, a lively destination offering entertainment, dining, and attractions. Stroll along the waterfront, take a ride on the Ferris wheel, or relax at one of the many parks while soaking in the stunning skyline.
  • Millennium Park: Discover the beauty of Millennium Park, an urban oasis featuring public art, gardens, and performance spaces. It's a great spot for families to enjoy outdoor activities, concerts, and the famous Cloud Gate sculpture, all while surrounded by the city's skyline.

Best time to go to Oak Street

The best time to visit Oak Street is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudySlightly LowSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnySlightly LowAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnySlightly HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighAverage
August73.0°F (22.8°C)Light RainMostly SunnySlightly HighAverage
September67.1°F (19.5°C)Light RainMostly SunnyAverageSlightly High
October54.9°F (12.7°C)Light RainMostly SunnyAverageSlightly High
November42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly CloudyAverageSlightly Low

The nearest major airports for your trip to Oak Street

Traveling to Oak Street, Chicago, can be conveniently done via its major airports. Chicago O'Hare International Airport (ORD) is approximately 24.1km away, with notable hotels nearby, including the 4.5-star Loews Chicago O'Hare Hotel and the 4-star Hyatt Regency O'Hare, both just 3.2km from the airport. Chicago Midway International Airport (MDW) is about 16.1km from Oak Street, featuring luxurious options like the 5-star Langham, Chicago and Nobu Hotel Chicago, located 8 and 14.5km away, respectively. For those considering Chicago Executive Airport (PWK), located 32.2km away, the 4.5-star Deer Path Inn is a comfortable choice just 16.1km away.

Frequently asked questions

What's the area like around Oak Street?
Oak Street is located in Chicago. This metropolitan area is known for its stunning architecture and top museums. If you're looking for a convenient place to stay, check out the 693 hotels and other accommodations you'll find within a mile.
What's the best place to stay close to Oak Street?
Adjacent to Oak Street, Four Seasons Hotel Chicago is one of the top choices for your stay based on our traveler data, and this hotel offers a full-service spa and a restaurant. Other good choices close by include The Chicago Hotel Collection Ambassador Gold Coast and Kasa Magnificent Mile Chicago.
How many hotels should I expect to find close to Oak Street?
Expedia has 693 hotels and other accommodations within a mile from Oak Street.
If I need to cancel the hotel reservation for my stay near Oak Street, will I receive a refund?
Yes! You'll find that most hotel reservations are refundable provided that you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of check in. If you booked a non-refundable reservation, you might be able to cancel it and be given a refund within a 24-hour period of booking. Enter your dates, click on "Search", then you can filter by "fully refundable" to review the top deals on offer near Oak Street.
Where can I learn more about changing or cancelling my trip in the area near Oak Street?
To access more information about picking new dates or cancelling your stay near Oak Street, click here.
What can I see and do near Oak Street?
You might want to spend some time browsing the exhibits at Museum of Contemporary Art Chicago, Chicago History Museum, or Art Institute of Chicago. Chicago Water Tower, Holy Name Cathedral, and Historic Michael Jordan Restaurant are some of the local landmarks to explore. You can watch performances at Broadway Playhouse, Second City, and House of Blues Chicago if you're interested in local theater.
How can I get to Oak Street?
With so many transportation options, seeing the area around Oak Street is a breeze. Take advantage of metro transit at State Station, Clark-Lake Station, and Lake Station. If you want to journey outside of the area, jump aboard a train from Millennium Station, Chicago Van Buren Street Station, or Chicago Union Station.