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Meet and greet in the hotel lobby before our adventure begins.
Start Time
Jul 9 12:30PM CDT
to
End Time
Jul 9 12:45PM CDT
Sheraton Grand Chicago Riverwalk, East North Water Street, Chicago, IL, USA
Back to Trip Details
Jul 9 - 12, 2026
Lyn Thompson Giles
Travel Designed By Lyn
lyn@traveldesignedbylyn.com
2157044077
Three-day weekend in Chicago exploring food, Obama legacy, Black entrepreneurship, fashion, and creative community spaces.
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 ...
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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...
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...
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...
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 .
Depart
11:15AM
1hr
Arrive
12:15PM
We will gather at luggage carousel .
Jul 9 – Jul 12 · Check in: 4:00PM
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...
12:30PM – 12:45PM · 15min
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...
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...
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 ...
9:30AM
30min
10:00AM
Meet in the lobby after breakfast.
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...
2:00PM
2:30PM
If you elect not to attend the shopping exploration you transfer will be back to the hotel.
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...
6:15PM
15min
6:30PM
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.
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...
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...
10:00AM – 4:00PM · 6hr
Vist Chicago's premier luxury, shopping, dinning and entertainment expeerience.
Enjoy the Taste of Chicago and sample local food culture.
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
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 ...
10:45AM – 11:00AM · 15min
Gather in hotel lobby for transfer to airport.
11:00AM
12:00PM
Meet in the lobby
2:31PM
2hr 22min
6:04PM