The Windy City: An Unforgettable Trip to Chicago, Experienced by Brightsun’s Managing Director

Direct from a travel expert, this is the tourist trip our Managing Director would recommend, based on his recent familiarisation trip there co-hosted by United Airlines, Choose Chicago, and Marriott hotels.

Take a long weekend break to Chicago and cover this incredible city in four days.

If you can, fly in the new United Polaris – United Airlines’ business class cabin which features amenities rivalling any first class. I found the cabin airy with many modern features including storage, charging points, Wi-Fi, a make-up mirror, and most importantly privacy cabins. The selection of TV programmes was extensive, with the latest releases, plus the selection of meals and beverages was of fantastic quality with three choices of accompanying white and red wines.

Meals include options for vegan passengers (also special meal orders could be placed 72 hours before departure). The cabin’s lie-flat bed, complete with Saks Fifth Avenue bedding, provided a comfortable place for me to sneak in a quick forty winks during the day and a good sleep on the return night flight. My first experience of Polaris is that United has significantly improved their game from the airline’s previous business class offering - you will be highly satisfied.

Where to Visit

Chicago is a hidden gem in the centre of the USA and apart from January and February when it is extremely cold, it is a year-round destination. I travelled in October, where you avoid the high prices and tourist crowds. The weather is a comfortable 18 degrees Celsius, with a jumper or light jacket needed during the evening. My tour on the first day started with an evening visit to the iconic 360 Chicago Observation Deck, offering breathtaking views of Chicago’s skyline, Lake Michigan, and the three surrounding states. After that you must follow in my footsteps and enjoy Chicago’s highest thrill ride – TILT, experiencing the exhilarating views from the 94th floor. To top it off, end the experience with a cocktail, enjoying a beautiful sunset over the Chicago skyline.

On my second day, the itinerary included a scenic river cruise, giving me the chance to witness the city’s famous landmarks and architectural marvels, and get an insight into Chicago’s history from the Great Fire of 1871 to becoming the birthplace of the skyscraper. After the cruise, I enjoyed a walking tour to explore the many neighborhoods of Chicago and learnt firsthand what it's like to live there. The day also included a visit to the lakefront Millennium Park, home to the iconic Cloud Gate statue aka “The Bean”. No Chicago experience is complete without a visit to the Art Institute, housing the greatest collection of paintings including works by Monet, Renoir, Dalí, Picasso, and Van Gogh.

On our third day, we stopped in to see the United Airlines management teams at their recently renovated offices located at the famous Willis Tower (formerly Sears Tower). I’m obviously a travel enthusiast and loved hearing the exciting update on United’s aggressive growth plan strategy, including an order of over 800 aircraft.  The next stop was the brand-new Chicago-centric Museum Skydeck Observation Deck displaying the best of the city's cuisine, history, culture, and architecture through immersive exhibits. I absolutely recommend taking the elevator to the 103rd floor for incredible and unobstructed views of the Chicago skyline. To end a fabulous day, we hit the theatre district for one of the hottest selling shows – Hamilton.

On our last day, after enjoying breakfast at the M Club in the hotel, we departed for a tour of the Field Museum, a must-see destination in Chicago home to Máximo the Titanosaur, the largest dinosaur ever discovered. From the ancient Egyptian tombs to over 10,000 years of Chinese history and culture, this museum offers a chance to delve into global history and is not to be missed.

Where to Eat

There are so many cool places to eat in Chicago and here are some recommendations from my trip:

For Breakfast:  Ed Debevec's

Start off your day with a visit to the famous retro-themed Ed Debevic’s, popular for its quirky waiters who serve food rudely to guests on purpose. The menu offered classic American breakfast options like fluffy pancakes, crispy bacon, and perfectly scrambled eggs.

Beatrix Streeterville

Another great option for breakfast, this restaurant’s innovative menu highlights healthy cooking with a combination of vegetarian entrées and comfort food dishes, from avocado toast with perfectly poached eggs to their signature fresh-squeezed juices.

For Lunch: Pazzo’s Chicago

With warm and rustic Italian décor, this restaurant seamlessly blends a charming ambiance with a delectable menu. The lunch menu features a wide array of options, from classic Italian sandwiches and fresh salads to heartwarming pasta dishes. The pleasant surroundings and attentive service make it an ideal spot for a midday meal.

Gino’s East

Gino's East offers a delightful experience in a true Windy City style. With three floors full of graffiti tagged walls, this restaurant boasts a beautiful rooftop terrace, the Gino’s East Wall of Fame, and The Comedy Bar – which features live performances all year long. The menu is a pizza lover's dream, featuring their iconic Chicago-style deep-dish pies with an array of mouth-watering toppings. From traditional classics to innovative creations, there is a pizza for every palate.

 
For Dinner: The Dearborn

Spread over 8,000-square-feet, this 225-seat restaurant has a sleek and contemporary design. The dinner menu features a diverse array of dishes that cater to various palates. We were quite surprised with the executive Chef Aaron Cuschieri’s eclectic twist on classic dishes like fish & chips and mac n cheese, and the heavenly desserts like chocolate tart and sticky toffee date cake left us craving for more.

Where to Stay

My stay at the Marriott Magnificent Mile in Chicago was classy, comfortable, and conveniently located, just a stone’s throw away from iconic attractions and shopping destinations. The hotel’s central location is ideal for conferences and leisure with many restaurants close by. Check-in was completed efficiently through the hotel’s app saving so much time. The room I stayed in was located on one of the higher floors, offering modern amenities such as a smart TV and high-speed Wi-Fi, plus stunning floor-to-ceiling windows with views of the Chicago skyline.

Culinary experiences at Marriott Magnificent Mile include the Chefs Table Experience, where produce from the hotel’s roof garden is used as part of their sustainability drive. There were many goodies provided by the Marriott including chocolates and bottles of honey; the hotel houses 900,000+ honeybees in beehives on its rooftop.

As my trip was co-hosted by United Airlines, on the return, I had the chance to experience both the Club Lounge and Polaris Lounge at Chicago O’Hare International Airport. The Club Lounge had all the amenities of a business class lounge, with adequately stocked food and drink and a nice selection available. The Polaris Lounge, being newer, had an aura of refined luxury, space, and comfort. The ideal way to relax before boarding the flatbed Polaris seat following an unforgettable long weekend in Chicago.     

Overall, this Chicago long weekend itinerary was captivating, giving me an opportunity to learn about the vast history, culture, food scene, and vibrant neighbourhoods of the city, and Brightsun Travel can offer that experience to you, whether it’s a solo trip, with friends, or with family. Brightsun offers return flights to Chicago starting from just £461 and for a 4-day long weekend holiday, we have exclusive packages with United Airlines from £869. To book a Chicago trip, call our travel specialists today!