The Best Way to Spend a Long Weekend in Chicago

The best way to spend a long weekend in Chicago

Short on time? That doesn't mean you can't get away from it all for a much needed break from everyday life. In fact, you can pack a lot of luxury into a weekend if you plan for it. The trick is to spend as little time as possible traveling and having as much fun as possible, because when time is limited, every second counts.

One of my favorite places for a getaway is Chicago. It feels close to home as it is easily accessible via O'Hare International Airport from almost any point in the United States. Stay in the city at an upscale hotel, and you'll be close to shopping, excursions, and dining galore, and the chic accommodations ensure you enjoy luxury throughout your trip.

Another way to optimize your stay is to plan an agenda to tick off the most important items on your must-see list. You do not know where to start? You're lucky! Ahead is an itinerary which, in my opinion, offers a taste of the best things the city has to offer.

Author's Note: Before booking your trip, I highly recommend that you check each location's website to view up-to-date information regarding COVID-19 restrictions and protocols.

Your Chicago weekend itinerary:

Saturday 1:00 p.m. - Lunch at Manny's Deli

Do you have time to waste before check-in? Grab a top stacked sandwich from Manny's Deli. A 15 minute drive from the hotel, this is the best Jewish deli I have ever seen - and it comes from a born and raised New Yorker! Try their Signature Ruben and Rice Ball Soup, you won't regret it (they have a mouthwatering breakfast menu too).

3:00 p.m. - Check-in at Thompson Chicago

I love hotels and consider myself a bit of a hotel snob. Since I prioritize style and luxury, the Thompson Chicago is my top choice. With exposed brick walls and plush velor furniture, the Thompson Chicago is both upscale and welcoming. I booked the 19th Floor Deluxe Junior Suite, which boasted chic decor with an equally lavish view. From my window, I could contemplate the tree-lined neighborhoods, the waterscape of the Great Lake and, of course, the city skyline.

4:00 p.m., Michigan Avenue coastal sightseeing tour

A short six-minute cab ride or 20-minute walk away you'll find Shoreline Sightseeing's Michigan Avenue dock, where boat tours depart almost once an hour. I boarded for a 1-hour architecture tour, which offers a unique view of Chicago's most famous buildings.

5.30 p.m. - Cocktails at Salone Nic o

Lucky for you, some of the best drinks in town can be found just a few floors from your hotel room. Before dinner, take a seat at the sultry Salone Nico, the lounge at Nico Osteria, which is located inside Thompson Chicago. Here you'll find light pre-dinner fare, a no-smother wine list with vintages from Italy and Greece, and classic cocktails (think: Palomas, Negronis, and Bee's Knees) that are well mixed.

7:00 p.m. - Dinner at the Blue Door Kitchen & Garden

Once the home of Chef Art Smith's Table Fifty-Two, the acclaimed cook (and former Oprah Winfrey personal chef) has reopened the space as a farm-to-table restaurant that prioritizes seasonal ingredients. and sustainability. With fresh food sourced from Midwestern farms - including the namesake Blue Door Farm, once owned by Winfrey - Chef Smith has put together a menu of comfort food with his artistic twist.

Some offerings: cornbread served with peaches, whipped cream and pecans; smothered macaroni and cheese in Mornay; buttermilk fried chicken with garlic mashed potatoes; shrimp and oatmeal with andouille and tomato stew; and for dessert, hummingbird pecan cake, coconut rumble and coulis.

9:30 p.m. - End of the night on the roof at J. Parker at the Lincoln Hotel

If you love the view from your hotel room, you will be enchanted by a clear view of Chicago through these panoramic windows. So, sit back and savor the views and a signature cocktail or two; Unique concoctions like Banana Matcha Gimlet and Getty's Herb with optional CBD bitters will intrigue your taste buds. Between the city lights and the intricate flavors, you'll want to sip slowly.

Sunday 10:00 am - Breakfast at Nico Osteria

Sleep, then descend to Nico Osteria Italian restaurant in Thompson Chicago for a decadent brunch to start the day. During my visit I ordered the Dungeness Crab and Poached Eggs over Focaccia, which I highly recommend if available. Otherwise, they have plenty of other gourmet options like lemon ricotta pancakes with blueberry sauce and Florentine eggs on a rosemary cookie with sautéed spinach.

11:00 a.m. Shopping at the Magnificent Mile

What luxury weekend is complete without a shopping spree worthy of madness? With the Magnificent Mile just a 10-minute walk away, spend a few hours browsing and shopping for top brands like Burberry, Tory Burch, Ugg and more. The Mile is also home to high-end retail shopping malls; explore the 900 shops of northern Michigan, the shops of North Bridge and Water Tower Place.

1:30 p.m. - Lunch at Lou Malnati pizzeria

On the way back to Thompson Chicago, stop at Lou Malnati's 1120 North State Street, which is practically next to the hotel. There, you'll enjoy legendary Chicago-style pizzas, well prepared.

After a quick lunch, you can drop off your bags and change for this afternoon's kayaking excursion.

3:00 p.m. - Architectural Kayak Tour of Chicago

Kayak Chicago's home port is just a 10-minute drive from the hotel and you'll head there for the late-afternoon architectural tour. With all experience levels welcome, you will learn Kayaking 101, including safety procedures and paddling before hitting the water. Once you're a pro, you'll be able to cruise along the Gold Coast for a leisurely look at the city's most important landmarks. The tour lasts three hours from start to finish.

7:30 p.m. - Dinner at MAKO Chicago

MAKO is a must stop for sushi lovers, especially after whetting up an appetite paddling along Lake Michigan. Opened by famous sushi chef BK Park, it offers an omakase menu. This means that the chef creates the dishes day after day, providing a truly unique dining experience. Drink pairing is also optional.

Because it's omakase style, you need to make reservations, and currently they are serving a limited capacity. You can also take your meal away and enjoy it in the comfort of your hotel room.

On Monday 9:00 am - Breakfast at The Original Pancake House

Even if it's your day of departure, you can still enjoy a leisurely breakfast. Located just across the street, The Original Pancake House is a neighborhood favorite and is open at 7:00 am if you're an early riser.

The local chain serves more than just pancakes; you will find fresh fruit juices, Belgian waffles, pancakes, hash browns, omelets, scrambles and more.

12:00 p.m. - Departure from Thompson Chicago

All good things must come to an end, but after a weekend full of shopping, sightseeing and dining, you'll feel as refreshed as if you had taken a much longer vacation.

You don't need a vacation far or long to experience the benefits of a change of scenery. Choose a hotel in a busy center and plan your program in advance. With a little planning, you can pack a lot of luxury into a short time for a fun and rewarding getaway.

Author's Note: Some stores, restaurants and destinations highlighted in this article may have different hours and procedures due to COVID-19 or may be temporarily closed. For this reason, I strongly suggest calling or checking each location's websites before planning your trip.

Eric Hrubant is the owner and president of CIRE Travel. CIRE Travel is a concierge style travel agency specializing in luxury vacations and honeymoons, once in a lifetime trips, as well as group and corporate travel. If you would like to be a guest blogger on A Luxury Travel Blog in order to enhance your profile, please contact us.