Start the morning at this well-loved bagel shop. Grab a freshly made bagel with your choice of toppings and a coffee — a simple, satisfying kick-off to the day. Highly rated at 4.6 stars.

Visit the Jazz Institute of Chicago, a non-profit organization dedicated to preserving and promoting jazz culture in Chicago. Explore their resources, programming info, and immerse yourselves in the city's rich jazz heritage — a perfect nod to your love of jazz and blues. Note: confirm hours in advance as they are not listed.

Head to Pizzeria Portofino ($$), a chic Italian eatery with a riverfront terrace and patio. Enjoy craft pizza, pasta, or grilled seafood alongside wines — outdoor riverside dining that's hard to beat for a relaxed midday meal. Highly rated at 4.8 stars.

Dinner at Kitchen + Kocktails by Kevin Kelley ($$) — a flashy lounge-style restaurant serving global comfort fare like fried chicken & waffles alongside creative cocktails. Rated 4.7 stars, this soul food gem is a lively, stylish way to spend your first evening in Chicago.

Optional evening cap at Sky Terrace Rooftop Lounge in the Streeterville neighborhood (1.4 km from downtown). This rooftop event venue offers elevated views of the city — a great spot to wind down Day 1 with drinks and skyline scenery. Note: confirm hours and access in advance as they are not listed. ~16 min from dinner.

Start the morning at this all-day café near Millennium Park. Grab a coffee and enjoy baked goods, breakfast items, or a light sandwich in a relaxed setting. Great spot to ease into the day.

🌟 Splurge highlight (one tier above budget). Enjoy creative global eats and tropical cocktails in a funky-ornate setting with coveted riverfront outdoor seats at Beatnik On The River. Perfect for outdoor dining lovers — watch the Chicago River while you dine.

⚠️ Note: Lincoln Hall is ~5 km north in Lincoln Park (~85 min transit). Hours are unconfirmed — verify before going. This highly-rated midsize live music venue is perfect for a dinner-hour show in an unpretentious atmosphere, with a cocktail bar on-site to pair with the evening.

Optional evening closer: Thee Jazz Rooftop at Wicker (~4 km from downtown, ~60 min from Lincoln Hall). Open 8 PM–11 PM — a live jazz rooftop event venue in Wicker Park. A fantastic cap to the day for jazz lovers who want to end the night under the sky with live music.

Dinner at Bar Mar.

Start Day 3 at this all-day café in the heart of the Loop. Grab baked goods, a breakfast sandwich, and a coffee to fuel the morning. Cozy and casual — a perfect low-key opener.

If you're up for a late-evening outing, head to The Salt Shed (~3.4 km away, ~15 min by rideshare) — a beloved Chicago live music and event venue with an impressive 4.7 rating. Check their schedule in advance for tonight's show. A fantastic cap to a Day 3 full of music, views, and great food. Verify event listings and hours before going.

Dinner at The Dearborn.

Start Day 4 at this all-day café on LaSalle. Grab freshly baked goods, breakfast items, and a coffee to ease into the morning. Relaxed counter-service vibe — perfect for a final morning in Chicago.

Settle in at Copper Club, a highly rated $$ restaurant and cocktail bar just a block away on W Madison St. Enjoy a relaxed midday meal with craft cocktails or coffee in a stylish setting — a great send-off lunch on your final day.

Head north (~7.6 km, ~30 min by transit) to Constellation on N Western Ave for an afternoon jazz or live music performance. This intimate open performance space showcases jazz, classical music, and dance events with a full bar. Check their schedule ahead of time for afternoon programming — a perfect fit for jazz and live music lovers wrapping up the trip. Note: hours not confirmed; verify event listings before visiting.

Dinner at Roanoke Restaurant.