The Boss Bar
18 min walk
from 311 S Wacker
6 min bike
via downtown streets
1449 m / 4754 ft
straight-line distance
77 places
within a 5-min walk
The Boss Bar is a bar at 420 North Clark Street, about 1449 m (18 min walk) from 311 South Wacker Drive. A solid choice for after-work drinks, catching a game, or starting a night out in downtown Chicago.
The Boss Bar sits in River North. The nearest CTA 'L' stop is Merchandise Mart (Brown & Purple lines), about a 3-minute walk, and Union Station's Metra and Amtrak trains are 18 minutes away on foot — so reaching it without a car is easy.
Map & Location
Dashed line shows the straight-line route to 311 South Wacker Drive (1449 m · ~18 min walk).
Getting to The Boss Bar
From 311 South Wacker Drive
Head north — it's about 1449 m on foot (18 min at a city pace). The dashed line on the map above shows the direction.
By 'L' Train
Ride to Merchandise Mart (Brown & Purple lines); from the platform exit it's roughly a 3-minute walk. A Ventra card or contactless bank card works on all CTA trains and buses.
From Union Station (Metra / Amtrak)
Exit toward Jackson Boulevard and walk 18 minutes; taxis and rideshare pickups are on Canal Street.
From the Airports
O'Hare: CTA Blue line to the Loop (~45 min) or 30–60 min by car. Midway: CTA Orange line to the Loop (~25 min) or about 20–30 min by car.
If You're Driving
The nearest public garage in this directory is 210 N Wells Self Park, about 6 min away on foot — reserve ahead through a parking app for the best rate, or see the 311 S Wacker parking guide.
Walking Times to Chicago Landmarks
| Chicago Riverwalk | 300 m | 4 min walk |
| Chicago Theatre | 580 m | 7 min walk |
| Millennium Park (Cloud Gate) | 1043 m | 13 min walk |
| Willis Tower & Skydeck | 1281 m | 16 min walk |
| The Art Institute of Chicago | 1311 m | 16 min walk |
| Chicago Board of Trade | 1339 m | 17 min walk |
| Union Station | 1450 m | 18 min walk |
| Buckingham Fountain | 1879 m | 23 min walk |
| Navy Pier | 1897 m | 24 min walk |
Everyday Essentials Near The Boss Bar
| Nearest coffee | Starbucks | 4 min walk |
| Nearest pharmacy | CVS Pharmacy | 1 min walk |
| Nearest bank branch | Chase | 1 min walk |
| Nearest public garage | 210 N Wells Self Park | 6 min walk |
| Nearest print/ship shop | The UPS Store | 5 min walk |
| Nearest dry cleaner | Shiny Cleaners | 13 min walk |
Within a 5-Minute Walk of The Boss Bar
Live counts from this directory — every link is a full detail page.
- 45 hotels: SpringHill Suites Chicago Downtown/River North, Residence Inn Chicago Downtown/River North, Hyatt Place Chicago / River North, Aloft Chicago Downtown River North (+41 more)
- 10 restaurants: Frontera Grill, Maggiano's Little Italy, Freshii, Harry Caray's Italian Steakhouse (+6 more)
- 1 cafes: Starbucks
- 1 attractions: Illinois Holocaust Museum Presents Experience360
- 2 entertainment: Celeste, Andy's Jazz Club & Restaurant
- 1 health & wellness: Thread Away
- 2 banks: Chase, Chase
- 1 pharmacies: CVS Pharmacy
- 1 print shops: The UPS Store
- 4 corporate services: Fort Dearborn Post Office, WeWork, Spaces, SPACE by doejo
The Neighborhood: River North
North of the Chicago River, River North mixes gallery-district polish with big-energy nightlife. Steakhouses, rooftop bars, design showrooms and the Merchandise Mart sit within a few minutes' walk of the Magnificent Mile's shopping.
Staying Overnight? Hotels Near The Boss Bar
The closest guest-rated hotels to this spot — live photos and ratings via Booking.com.
★ 8.6/10 · 651 reviews · 2 min walk from here
Check Rates
★ 8.9/10 · 1257 reviews · 2 min walk from here
Check RatesMake an Outing of It
A visit to The Boss Bar pairs naturally with the blocks around it. Then start with Illinois Holocaust Museum Presents Experience360 (3 min away). Then continue with Frontera Grill (1 min away). Then continue with Starbucks (4 min away). All three have full detail pages in this directory with maps and walking times.
Good to Know: Local Tips
After-work happy hour (roughly 4:30–6:30pm) is the Loop's busiest bar window — arrive by 5pm for a table. Illinois bars card everyone who looks under 40, so carry ID, and note that many Loop taverns close earlier on Sundays.
Frequently Asked Questions
How far is The Boss Bar from 311 South Wacker Drive? +
The Boss Bar is about 1449 meters from 311 South Wacker Drive — roughly a 18-minute walk through downtown Chicago.
What is the nearest CTA 'L' station to The Boss Bar? +
The closest 'L' stop is Merchandise Mart (Brown & Purple lines), about 262 m away — a 3-minute walk.
What else is within a short walk of The Boss Bar? +
Within about five minutes on foot you'll find 11 other places to eat or grab coffee, plus more bars, shops and attractions — see the "within a 5-minute walk" section on this page.
More Bars & Pubs Nearby
The Baton Show Lounge
436 North Clark Street
19 min from 311 S Wacker
La Mez Agave Lounge
108 West Kinzie Street
17 min from 311 S Wacker
Enolo Wine Cafe
450 North Clark Street
19 min from 311 S Wacker
O'Callaghan's
29 West Hubbard Street
19 min from 311 S Wacker
Jojo's Shake Bar
23 West Hubbard Street
19 min from 311 S Wacker
Bar Louie
333-335 North Dearborn Street
17 min from 311 S Wacker
Other Places Near The Boss Bar
Celeste
111 West Hubbard Street
18 min from 311 S Wacker Entertainment
Chase
401 North Clark Street
18 min from 311 S Wacker Banks
Frontera Grill
445 North Clark Street
19 min from 311 S Wacker Restaurants
CVS Pharmacy
121 West Kinzie Street
17 min from 311 S Wacker Pharmacies
SpringHill Suites Chicago Downtown/River North
410 North Dearborn Street
18 min from 311 S Wacker Hotels
Residence Inn Chicago Downtown/River North
410 North Dearborn Street
18 min from 311 S Wacker Hotels