Laughter & Late-Night Blue Notes

The transition from Chicago’s Old Town to River North is more than a 2-mile walk; it is a pilgrimage through the city’s primary cultural exports. The night begins at The Second City, a venue that has functioned as the definitive farm system for global comedy for decades The Best of The Second C…. Securing premium seating here is not merely about comfort; it is about positioning for the front-row crowd work that often yields the night’s most spontaneous brilliance. While the main stage revues are polished and punchy, the true insider move is staying for the free improv set immediately following the performance Second City (2026) - All…. These sets are where the next generation of Saturday Night Live stars test their limits without the constraints of a script Chicago Shows. Transitioning from the high-energy theater of Old Town to the jazz basements of River North requires a brisk walk south, ideally cutting through the Gold Coast to admire the city’s well-preserved architecture The Best Things to Do in…. The destination is Andy’s Jazz Club, one of the few remaining institutions that has stubbornly resisted the urge to sanitize the Chicago jazz experience. It is a dual-threat venue: the acoustics are sharp enough for the aficionados, yet the kitchen produces a Chicken Vesuvio—a garlic-heavy, potato-laden Chicago staple—that rivals the city's best Italian red-sauce joints. To properly close the night, movement shifts two blocks east to Blue Chicago. This is not a venue for sitting quietly and dissecting a bass solo; it is a high-octane blues sanctuary designed for kinetic energy. The room is intimate, the drink menu is secondary to the music, and the dance floor is non-negotiable once the late-night set kicks in Top things to do in Chic…. It represents the gritty, unpretentious soul of the Chicago sound, stripped of any tourist-trap artifice.

What to Expect

The evening spans roughly six hours. Second City tickets should be purchased weeks in advance, particularly for the main stage shows Second City (2026) - All…. The walk from Old Town to Andy’s is approximately 1.8 miles and takes 35 minutes; ride-shares are plentiful if weather is prohibitive, but walking allows for better architectural viewing. Blue Chicago requires a cash cover at the door and operates with an old-school bar policy—bring plenty of physical currency to avoid high-fee ATMs on-site. Dress is 'Chicago casual,' meaning blazers are welcome but jeans are the standard uniform.

The Route

1

The Second City

71

Navi Walkability Score

Path Popularity14

Infrastructure54

Terrain100

Safety73

Lighting99

Amenities96

Transit50

"Spring for the premium tickets to snag a front-row seat for the best crowd work, and stick around for the free improv set after the main show—it's usually the funniest part of the night."

30-45 min34 min

34 min · 1.8 mi71

2

Andy's Jazz Club & Restaurant

71

Navi Walkability Score

Path Popularity14

Infrastructure54

Terrain100

Safety73

Lighting99

Amenities96

Transit50

"Grab a seat at the bar for the best view of the jam sessions and don't sleep on the Chicken Vesuvio; it's surprisingly elite for a jazz joint."

30-45 min7 min

7 min · 553 m82

3

Blue Chicago

82

Navi Walkability Score

Path Popularity50

Infrastructure63

Terrain100

Safety79

Lighting100

Amenities92

Transit80

"Bring plenty of cash for the cover and the bar to avoid the ATM fees, then get straight to the dance floor for the best late-night energy in the city."

45 min - 1 hr7 min walk

Frequently Asked Questions