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Taste of Chicago: July 9-12, 2026

Jul 9 - 12, 2026

Your Advisor

Lyn Thompson Giles

Travel Designed By Lyn

lyn@traveldesignedbylyn.com

2157044077

Ready to Book?? Click HERE!!

Full Itinerary Daily Overview Pricing Documents

Overview

Three-day weekend in Chicago exploring food, Obama legacy, Black entrepreneurship, fashion, and creative community spaces.

Trip Details

Important Update: Obama Presidential Center

Dear Travelers, We are looking forward to sharing an amazing Chicago experience with you and wanted to provide an important update regarding one portion of our itinerary. As many of you know, the planned visit to the Obama Presidential Center was ...

Chicago Preview

Climate & Seasons Late spring in Chicago (around early July timing for Taste of Chicago) usually brings warm, humid days and comfortable evenings with lake breezes — perfect for outdoor festivals like Taste of Chicago at Grant Park. Pack layers fo...

Details & Pricing

Cost (based on 2 people in a room): Hotel + Economy Airfare $2,550 per room/ $1,275 per person Deposit $550 per person Hotel + Business Airfare $2,831 per room/ $1,415 per person Deposit $850 per person Due Dates: Deposit NOW (lock in the best pri...

Packing List

Essential Documents & Money You'll want quick access to the basics so you can move through check-in, rideshares, and bar/restaurant tabs without fuss. Photo ID (driver's license or passport) — Chicago venues commonly check ID for 21+ entry. Credit...

Day 1 · Thu, Jul 9 · Chicago

Flight from PHL to ORD (UA1811)

PHL

8:08AM

2hr 29min

ORD

9:34AM

Additional baggage charges may apply. † indicates codeshare flight. Flight prices are subject to change based upon availability .

Transfer Airport to Hotel

Depart

11:15AM

1hr

Arrive

12:15PM

We will gather at luggage carousel .

Sheraton Grand Chicago Riverwalk

Jul 9 – Jul 12 · Check in: 4:00PM

https://www.marriott.com/en-us/hotels/chigs-sheraton-grand-chicago-riverwalk/overview/?scid=f2ae0541-1279-4f24-b197-a979c79310b0

We will be leaving our luggage with bell hop for security. Breakfast Included Includes Breakfast for Two. Guests will receive up to 2 breakfasts daily per room. Single occupancy will receive 1 breakfast daily per room. Additional adults and childr...

Travel Insurance

Kick Off

12:30PM – 12:45PM · 15min

Meet and greet in the hotel lobby before our adventure begins.

Taste of Chicago (Food Festival Experience)

12:45PM – 4:00PM · 3hr 15min

Overview Taste of Chicago is Chicago’s iconic summer food festival showcasing the city’s diverse culinary scene — from deep-dish pizza and Polish sausages to Michelin-level chef creations and inventive street-food bites. Entry is free however, foo...

Chicago Riverwalk Visit

4:30PM – 6:30PM · 2hr

Overview The Chicago Riverwalk is a pedestrian waterfront located along the south bank of the Chicago River in downtown Chicago. It stretches approximately 1.25 miles and links Lake Shore Drive to Franklin Street, offering a sequence of public spa...

Rooftop Bar near Riverwalk

7:30PM – 10:00PM · 2hr 30min

Let's meet share the view of Chicago's skyline. Overview Below are rooftop bar experiences located near the Riverwalk area. Each entry includes a brief description of the vibe, typical highlights, and what to expect. These are curated suggestions ...

Day 2 · Fri, Jul 10 · Chicago

Transportation to Bronzeville Area of the City

Depart

9:30AM

30min

Arrive

10:00AM

Meet in the lobby after breakfast.

Bronzeville & Beyond: A Curated Black Chicago

10:00AM – 2:00PM · 4hr

Black Chicago: Culture, Legacy & Style Overview Discover the heart and soul of Black Chicago during this curated cultural experience through Bronzeville and Pullman—two neighborhoods deeply connected to the stories of migration, resilience, creati...

Transportation to Silver Room for iconic black shopping

Depart

2:00PM

30min

Arrive

2:30PM

If you elect not to attend the shopping exploration you transfer will be back to the hotel.

Curated Chicago: Culture, Style & Sisterhood

2:30PM – 6:00PM · 3hr 30min

Overview Explore the creative energy, cultural richness, and distinctive style of Chicago’s South Side during this curated shopping and cultural experience through Hyde Park and surrounding neighborhoods. Designed to blend fashion, art, literature...

Transportation to Sheraton Riverwalk Hotel

Depart

6:15PM

15min

Arrive

6:30PM

Meet in the lobby after breakfast.

Taste of Chicago

2:30PM – 6:00PM · 3hr 30min

Enjoy the Taste of Chicago and sample local food culture. If you would prefer not to visit Hyde Park feel free to return to the festival. We will provide transfers.

Suggested: Dinner and Jazz Evening

7:30PM – 11:59PM · 4hr 29min

End the day with dinner and a jazz evening in Chicago. We have two options for you to select from. This evening is for you to dine and explore at your own pace . This evening is a guests' own expense. Andy’s Jazz Club (~5 min walk): A popular, his...

Day 3 · Sat, Jul 11 · Chicago

Optional: Wellness Experience

9:00AM – 12:00PM · 3hr

Choose between Allyu Spa or milk+honey spa, please make your appointments between 9am - 12noon. Option 1 - Allyu Spa About 5–7 minute Uber / ~15 minute walk Vibe: Zen, globally inspired (Moroccan/Thai energy) More intimate and tranquil Please make...

Magnificent Mile Chicago

10:00AM – 4:00PM · 6hr

Vist Chicago's premier luxury, shopping, dinning and entertainment expeerience.

Visit "The Bean" in Millennium Park

10:00AM – 4:00PM · 6hr

Taste of Chicago

10:00AM – 4:00PM · 6hr

Enjoy the Taste of Chicago and sample local food culture.

Optional: Coffee at Sip & Savor

12:00PM – 4:00PM · 4hr

Cultural Book & Coffee Moment 📖 Semicolon Bookstore & Gallery A Black woman-owned independent bookstore featuring: Black literature Social justice works Community-centered programming

Chicago Riverwalk Visit

4:30PM – 6:30PM · 2hr

Overview The Chicago Riverwalk is a pedestrian waterfront located along the south bank of the Chicago River in downtown Chicago. It stretches approximately 1.25 miles and links Lake Shore Drive to Franklin Street, offering a sequence of public spa...

Farewell Dinner at Kitchen + Kocktails by Kevin Kelley

7:30PM – 10:30PM · 3hr

Vibe: Upscale Black-owned dining + great energy Why this is a standout for your group: Southern-inspired elevated comfort food Beautiful atmosphere for a “last night” feel Great cocktails + music + vibe Dinner will be price fixed. Drinks are a la ...

Day 4 · Sun, Jul 12 · Chicago

Check Out Hotel

10:45AM – 11:00AM · 15min

Gather in hotel lobby for transfer to airport.

Transfer Hotel to Airport

Depart

11:00AM

1hr

Arrive

12:00PM

Meet in the lobby

Flight from ORD to PHL (UA2430)

ORD

2:31PM

2hr 22min

PHL

6:04PM