Have your trip to Chicago planned by a professional
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Looking to spend a holiday or weekend in the Windy City. Use this guide to plan ahead for your trip.

Hyatt Regency Hotel
To start the weekend off, I checked into the Hyatt Regency Chicago, which is a luxurious hotel located in downtown Chicago, right on the Chicago River. The hotel boasts spacious and modern rooms with stunning views of the city and the river. Guests can enjoy a range of amenities, including a 24-hour fitness center, an indoor pool, and multiple dining options, including a restaurant with a seasonal outdoor terrace.
The hotel is in close proximity to popular tourist attractions such as Millennium Park, the Magnificent Mile, and Navy Pier, making it a convenient location for both business and leisure travelers.. From the stunning views of the skyline to the luxurious amenities, it was the perfect home base for my trip.
Accommodations at Hyatt Regency Chicago
The hotel features a variety of rooms and suites to suit every traveler’s needs. Here are some of the rooms and their descriptions:
Standard Rooms: These rooms feature a king or two double beds, a flat-screen TV, a work desk, and a seating area. The rooms offer stunning views of the city or the Chicago River.
Suites: The suites at Hyatt Regency Chicago are spacious and elegant, offering separate living areas and private bedrooms. The suites feature a king-size bed, a flat-screen TV, a work desk, and a seating area. The suites offer stunning views of the city or the Chicago River.
Club Rooms: These rooms offer access to the Regency Club Lounge, which offers complimentary breakfast, evening hors d’oeuvres, and a private space to work or relax. The rooms feature a king or two double beds, a flat-screen TV, a work desk, and a seating area.
Deluxe Rooms: These rooms offer additional space and luxurious amenities, including a spa-like bathroom with a rain shower and a soaking tub. The rooms feature a king-size bed, a flat-screen TV, a work desk, and a seating area.
Executive Suites: These spacious suites feature a separate living area, a private bedroom with a king-size bed, a spa-like bathroom with a rain shower and a soaking tub, and stunning views of the city or the Chicago River.
Whether you’re traveling for business or pleasure, Hyatt Regency Chicago has a room that will exceed your expectations.
Exploring Chicago's Culinary Scene: A Weekend of Delicious Eats
Chicago is known for its world-class food scene, with diverse culinary offerings that cater to every palate. From deep-dish pizza to artisanal coffee shops and Michelin-starred restaurants, the Windy City has it all. If you’re planning a weekend getaway to explore Chicago’s food scene, you’re in for a treat. With so many options to choose from, it can be overwhelming to decide where to start.
I’ve put together a list of must-try restaurants and food experiences to help you make the most of your culinary adventure in Chicago. So, get ready to indulge in delicious eats and experience the unique flavors of Chicago.
Stetsons Modern Steak + Sushi
Stetsons Modern Steak + Sushi, the restaurant located inside the Hyatt Regency Chicago, offers an innovative and sophisticated dining experience. The menu features prime steaks, fresh sushi and sashimi, and a variety of globally inspired dishes made with locally sourced ingredients.
Their extensive wine list, creative cocktails, and craft beer selection provide perfect pairings for any meal. With its chic and inviting atmosphere and impeccable service, Stetsons is the perfect spot for a business lunch, a romantic dinner, or a night out with friends.
Wishbone
Wishbone is a popular restaurant in Chicago that specializes in Southern-style cuisine. The menu features classic dishes such as biscuits and gravy, jambalaya, gumbo, and shrimp and grits. They also offer a variety of salads, sandwiches, and entrees, including BBQ ribs and grilled salmon.
In addition to their food offerings, Wishbone also has an extensive drink menu, including a range of craft beers, specialty cocktails, and wines. The restaurant has a cozy and casual atmosphere, with friendly service and a welcoming vibe. Whether you’re in the mood for a hearty brunch or a satisfying dinner, Wishbone is a great choice for Southern comfort food in Chicago.
Here are some of the notable restaurants in Chicago that you should try while there:
Alinea: Alinea is a three-Michelin-starred restaurant that offers a unique and immersive dining experience. The restaurant features a 20-course tasting menu that showcases Chef Grant Achatz’s innovative and creative approach to modern cuisine.
Girl & the Goat: Chef Stephanie Izard’s Girl & the Goat is a lively restaurant that offers a delicious and creative menu of shareable plates. The menu features a mix of meat, fish, and vegetarian dishes, with bold flavors and unique combinations.
Lou Malnati’s Pizzeria: No trip to Chicago is complete without trying the city’s famous deep-dish pizza. Lou Malnati’s Pizzeria is a must-visit spot for pizza lovers, serving up delicious and iconic Chicago-style pizza for over 50 years.
Au Cheval: Au Cheval is a popular diner-style restaurant that offers a range of classic American dishes with a gourmet twist. The menu features delicious burgers, fried chicken, and other comfort food favorites, all made with high-quality ingredients.
The Publican: The Publican is a farm-to-table restaurant that offers a unique and seasonal menu of meat, fish, and vegetable dishes. The restaurant’s communal tables and lively atmosphere make it a great spot for a casual and delicious meal with friends.
These are just a few of the many notable restaurants in Chicago that you should try while there. With so many options to choose from, you’re sure to find something that suits your taste and budget.
A Guide to the Chicago's Top Attractions and Activities
Chicago is a vibrant city with a rich history and a diverse range of attractions and activities to explore. From iconic landmarks and world-class museums to delicious food and exciting nightlife, there’s something for everyone in the Windy City. Whether you’re visiting for the first time or are a seasoned traveler, Chicago is a city that never disappoints.
I’ll take you through some of the top attractions and activities that the city has to offer, helping you make the most of your time in Chicago.
Here’s a quick summary of the top attractions and activities that you should see and do while in Chicago:
Visit the Skydeck at Willis Tower and take in stunning views of the city.
Explore the Art Institute of Chicago and discover its impressive collection of artwork.
Take a stroll through Millennium Park and marvel at the iconic Cloud Gate sculpture.
Indulge in the city’s famous deep-dish pizza at Lou Malnati’s Pizzeria.
Enjoy a night out at one of Chicago’s famous blues clubs.
Take a riverboat tour and learn about the city’s rich history and architecture.
Catch a Chicago Cubs game at Wrigley Field.
These are just a few of the top attractions and activities that you can enjoy while in Chicago. With so much to see and do, you’re sure to have an unforgettable experience in the Windy City.
Final Thoughts on a fun filled weekend in Chicago
In conclusion, my Memorial Day Weekend trip to Chicago was everything I had hoped it would be and more. From the stunning views at the Skydeck to the delicious deep-dish pizza and the city’s famous blues clubs, Chicago did not disappoint. I was blown away by the city’s rich history, culture, and friendly people. I can’t wait to return to Chicago and continue exploring all that this amazing city has to offer.
So, if you’re looking for a fun and exciting destination for your next trip, I highly recommend putting Chicago on your list. Trust me, you won’t regret it!