2027 Spring Fling To Chicago

Chicago Cultural & Dining Getaway (May 27-30, 2027)

Introduction
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Chicago / May 27-30, 2027

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Chicago Cultural & Dining Getaway (May 27-30, 2027)

Experience the vibrant culture and renowned dining scene of Chicago over four days. Enjoy curated tours, upscale dining, riverboat excursions, and time to explore the city’s sights, shopping, and nightlife at your own pace.

About This Trip

There are cities you visit—and then there are cities you experience.

Chicago is one of those cities.

May 27–30, 2027, The Melting Pot Dining Club is heading to the Windy City for our Chicago Spring Fling Culinary & Cultural Experience—a long weekend created around incredible food, beautiful city views, culture, connection and a few unforgettable experiences along the way.

For three nights and four days, we’ll make downtown Chicago our home while enjoying a thoughtfully curated blend of upscale dining, sightseeing, culture and time to simply enjoy the city.

We’ll gather around beautiful tables for memorable dining experiences, cruise the Chicago River surrounded by some of the most celebrated architecture in America, explore the culture and history of this remarkable city, and leave a little room to discover Chicago at your own pace.

This isn’t simply another weekend getaway.

It’s a culinary escape.

A cultural experience.

A spring adventure.

And another opportunity to create incredible memories with an amazing community of people who believe some of life’s best moments happen around the table—and along the journey.

What You Can Expect

Imagine waking up in the heart of downtown Chicago with an entire city waiting outside your door.

Mornings may begin with coffee, breakfast and a leisurely start before heading out to explore.

During our stay, we’ll experience Chicago from several different perspectives—from its celebrated culinary scene to its iconic skyline, architecture, neighborhoods and cultural landmarks.

We’ll gather for two specially selected upscale fine dining experiences, giving us the opportunity to experience some of the incredible cuisine that has helped make Chicago one of America’s great food cities.

We’ll take to the water for a Chicago River cruise, where the city’s legendary architecture becomes the backdrop to an unforgettable afternoon.

And we’ll experience a thoughtfully selected cultural excursion, with hopes of including an opportunity to experience the Obama Presidential Center as part of our Chicago journey, subject to opening, availability and final scheduling.

But just like every Melting Pot Dining Club experience, there will also be time for you to make the trip your own.

Time to shop.

Time to explore.

Time to discover a great Chicago restaurant or cocktail lounge.

Time to take a walk along the river.

Time to reconnect with old friends—or make new ones.

And perhaps time for a few surprises we haven’t told you about yet.

The Culinary Experience

Chicago is a city that knows how to eat.

From celebrated chefs and elegant dining rooms to neighborhood institutions and cuisine influenced by cultures from around the world, food is woven into the identity of this city.

Naturally, it will be at the heart of our Spring Fling.

Our weekend will include two amazing upscale fine dining experiences, thoughtfully selected to give our guests an opportunity to gather, connect and experience Chicago through its culinary scene.

Expect beautiful settings.

Exceptional cuisine.

Great conversation.

A toast or two.

And the kind of dinners where nobody is quite ready to leave the table.

Some of the details may be announced before we arrive.

Others just might remain a surprise.

Because if you’ve traveled with The Melting Pot Dining Club before, you already know:

Sometimes not knowing exactly what’s coming next is part of the fun.

The Chicago Experience

There is something special about Chicago in the spring.

The city comes alive.

The river winds between towering architectural landmarks. Sidewalk cafés begin filling. The lakefront calls. And everywhere you turn, another neighborhood, restaurant, museum, shop or landmark invites you to explore.

One of the highlights of our weekend will be experiencing Chicago from the river on a Riverboat Cruise Tour, offering spectacular views of the city’s famous skyline and architectural treasures.

We’ll also enjoy a cultural excursion designed to introduce us to another side of Chicago—its people, history and influence.

And in between our planned experiences, you’ll have an opportunity to discover a little of the city for yourself.

Chicago has plenty waiting for you.

Our Home in Chicago

For three nights, we’ll settle into Hotel Chicago, placing us in the heart of the city and close to dining, entertainment, shopping and many of Chicago’s most recognizable attractions.

After full days of exploring—and memorable evenings around the table—you’ll have a comfortable place to return, relax and recharge for whatever the next day brings.

And because this is a Melting Pot Dining Club experience, we’ve taken care of many of the details so you can spend less time coordinating and more time enjoying Chicago.

Getting There

Guests will fly into one of Chicago’s major airports:

Chicago O’Hare International Airport (ORD)

or

Chicago Midway International Airport (MDW)

Round-trip airport transportation is included during designated arrival and departure windows.

Prior to the trip, registered guests will receive detailed travel information, recommended flight arrival and departure windows, airport transportation instructions, packing suggestions and other important details to make your arrival as seamless as possible.

Book your flight.

Pack your bags.

Meet us in Chicago.

We’ll take it from there.

What’s Not Included

Airfare

Flights to and from Chicago are NOT included.

Guests are responsible for booking their own airfare.

Meals Not Listed

Meals outside of the designated included dining experiences are the responsibility of each guest unless otherwise stated in the final itinerary.

Travel Insurance

Travel insurance is strongly recommended to protect your trip investment against unexpected circumstances.

Personal Expenses

Shopping, souvenirs, cocktails, additional transportation, entertainment and other personal purchases not specifically listed as part of the package are not included.

Optional Experiences

Any activities, tours, dining experiences or services identified as optional or outside the official itinerary will be at the guest’s expense.


Deposit & Payments

Your deposit secures your reservation and is non-refundable.

Flexible payment arrangements are available, making it easier to reserve your place now and spread the cost of your Chicago experience over time.

Space for this experience is limited, and reservations will be confirmed on a first-come, first-served basis.

Guests should carefully review all payment, cancellation and travel policies before reserving.

Come Experience Chicago With Us

For four incredible days, we’re trading the ordinary for something a little more exciting.

We’re trading routine for discovery.

Regular dinners for beautiful tables and unforgettable cuisine.

The everyday commute for a cruise along the Chicago River.

And another ordinary weekend at home for springtime in one of America’s most exciting cities.

Come because you love food.

Come because you love travel.

Come because you’ve been waiting to experience Chicago.

Come for the culture.

Come for the architecture.

Come for the friendships and connections.

Or simply come because you deserve a great weekend away.

Whatever brings you to Chicago, our hope is that you return home with wonderful memories, new friendships, incredible stories—and already wondering:

Where is The Melting Pot Dining Club taking us next?

May 27–30, 2027

Chicago, Illinois

Cuisine. Culture. Connection. Discovery.

Welcome to the Chicago Spring Fling.

Trip Highlights

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At a glance

Thursday, May 27, 2027

Friday, May 28, 2027

Saturday, May 29, 2027

Sunday, May 30, 2027

Thursday, May 27, 2027

Day 1 - Airport Arrivals and Hotel Check-in

27-May-2027
Day 1 - Airport Arrivals and Hotel Check-in image

Arrive in Chicago and Settle In

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Airport Arrivals & Hotel Check-in

Arrive in Chicago and check in to your hotel.
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Dinner on your own

Everyone on their own for dinner, sightseeing, and nightlife activities.
Friday, May 28, 2027

Day 2 - Chicago Cultural Tour and Dining

28-May-2027
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Cultural Tour, Shopping, and Upscale Dining

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Breakfast on your own

Everyone on their own for breakfast.
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Cultural Tour & Lunch at Cultural Attraction Location

11:00am- Cultural Tour & Lunch at Cultural Attraction Location (Obama Center pending).
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Sight Seeing & Shopping

2:00pm- Sight Seeing & Shopping (everyone on their own).
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Upscale Dining Experience-One

7:00pm-9:30pm- Upscale Dining Experience One (Restaurant TBA).
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After Hours Entertainment

9:30pm- After Hours Entertainment (everyone on their own).
Saturday, May 29, 2027

Day 3 - Chicago Riverboat Tour and Dining

29-May-2027
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Riverboat Tour, Shopping, and Jazz Supper Club

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Breakfast on your own

Everyone on their own for breakfast.
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Riverboat Tour

11:00am-Riverboat Tour (exact tour time TBA).
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Sight seeing & Shopping

2:00pm-Sight seeing & Shopping (everyone on their own).
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Upscale Dining Experience-Two @ Tortoise Jazz & Supper Club

7:00pm-10:30pm-Upscale Dining Experience Two @ Tortoise Jazz & Supper Club.
Sunday, May 30, 2027

Day 4 - Airport Departures and Farewell

30-May-2027
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Departures and Final Meals in Chicago

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Airport Departures

Airport Departures.
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Breakfast & Lunch on your own

Everyone on their own for breakfast & Lunch (depending on flight times).
Map of the trip locations

Map

A. Tortoise Supper Club

350 N State St, Chicago, IL 60654
© 2026 Retreats by Nala