Logan Square Dinner & Jazz

Logan Square$$4 hoursEvening
~$136 for two
Get directions to all stops
Walk

Logan Square Boulevard

Walk the tree-lined boulevard past greystones and the Illinois Centennial Monument. This is one of Chicago's most beautiful neighbourhoods.

$0 pp20 minLogan Blvd & N Kedzie Ave, Chicago, IL 60647
Lula Cafe
2
Meal

Lula Cafe

5 min walk. Farm-to-table pioneer since 1999. The Monday pasta night is legendary — handmade pasta, prix fixe, always packed. Book ahead.

$35 pp1 hr 15 min2537 N Kedzie Ave, Chicago, IL 60647
Lost Lake
3
Drinks

Lost Lake

5 min walk. Tropical tiki bar that takes its cocktails seriously. Paul McGee's rum drinks are some of the best in the country. The vibe is fun and colourful.

$18 pp1 hr3154 W Diversey Ave, Chicago, IL 60647
Rosa's Lounge
4
Activity

Rosa's Lounge

10 min walk. No-frills blues club where Chicago blues is still alive. Live music every night, cheap drinks, real deal. An authentic Chicago experience.

$15 pp1 hr 30 min3420 W Armitage Ave, Chicago, IL 60647
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Couples visiting Chicago typically stay 2–3 nights

Comments

TwoTonight TeamStaffMar 2026

Rosa's Lounge is the real deal — no tourists, no gimmicks, just incredible blues musicians. Get there early for a good seat.

Total (for two)~$136
Duration4 hours
Best For

Couples

Best Time

Weekend

Tags

Best Seasons

All Year

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