A Weekend in Chicago: The Luxury Edition

By the numbers, Chicago is pretty impressive. Chicago is the 3rd largest city in the United States with over 60 museums, 600 parks, and nearly 9000 acres of green space. Chicago has 28 miles of lakefront, 24 beaches, over 7000 restaurants, and almost 200 breweries. Chicago has all this and more within its 234 square miles.

We have just one word for you, Chicago—wow.

Looking for ideas on how to spend a luxurious weekend in Chicago? While a weekend will be enough time to get a taste of Windy City, if you have more to spare, you won’t regret it.

Why go to Chicago?

Chicago is one of the most easily accessed cities in the United States, making it popular for tourism. How’s this for a number? In 2022, nearly 50 million people visited Chicago—up 60% from 2021. But don’t worry, there are enough hotels in Chicago for everyone. The best restaurants in Chicago are ready and waiting for you to arrive. So is the team at CIRE. They can help you plan a Chicago itinerary that suits your needs to perfection.

Ready to take on Chicago? Let’s start adding some ideas to your list, luxury-style.

Where to Stay: The Best Luxury Hotels in Chicago

Chicago is chock full of luxury hotels. Some have dazzling waterfront views. Some have world-class spa and wellness programs. Others have Michelin-starred restaurants to tempt the most refined palettes. Choosing the best hotel is about finding one that suits your travel style best. We’ve rounded up a few favorite luxury hotels in Chicago so you can discover the right one for your stay.

The Pendry
Vibe: Next-gen modern with gilded-age elegance.
The Loop.
Restaurant: Contemporary French dining at Venteux.
Best Amenity:
24-hour fitness center featuring Peloton bikes.
Unique Selling Point:
Set within the iconic 1929 Art Deco Carbide and Carbon Building.

The Chicago Athletic Association Hotel
Vibe: Traditional, classic, and sophisticated old-world charm.
Millennium Park.
Restaurant: Cindy’s Rooftop Restaurant—known for its craft cocktails and fresh seafood.
Best Amenity:
Game room with foosball and a historic basketball court. The uber-clubby Cherry Circle Room restaurant.
Unique Selling Point:
Cindy’s year-round terrace will wow guests with unparalleled city views.

The Peninsula
Vibe: Midwestern hospitality paired with ultra-luxury service.
Magnificent Mile.
Restaurant: Shanghai Terrace exudes a 1930s Supper Club vibe.
Best Amenity:
Sun Terrace with dramatic skyline views.
Unique Selling Point:
The 18th-floor Peninsula Suite hovers over the city. It has highly-curated touches of luxury and a wraparound terrace overlooking Lake Michigan.

The Langham
Vibe: Urban sophistication and refined luxury.
Magnificent Mile.
Restaurant: Travelle for breakfast, brunch, and lunch serves ingredients from farms, ranches, and orchards. Lite bites for dinner are served at the window-framed Travelle Lounge.
Best Amenity: Private cinema movie night for up to six guests with a 111-inch screen in the cinema suite—complete with buttery popcorn and red-carpet culinary treats.
Unique Selling Point:
Set within a 52-story landmark tower originally designed by famed architect Mies van der Rohe.

The Hoxton
Vibe: Convivial and relaxed atmosphere with playful artisan touches.
Fulton Market.
Restaurant: Cabra Cevicheria is The Hoxton’s Peruvian-inspired rooftop gem.
Best Amenity: The rooftop pool is one of Chicago’s only rooftop pools.
Unique Selling Point:
Walking distance to some of the city’s hottest restaurants makes The Hoxton an excellent location for foodies.

Where to Eat: The Best Restaurants in Chicago

A cosmopolitan city like Chicago has restaurants that cater to all appetites. From casual and traditional deep-dish pizza to fancy prix-fixe tasting menus with wine pairings. When it comes to dining—Chicago delivers. Some of our current favorites follow. You will undoubtedly be raving about them long after the meal has ended.

Cuisine: Contemporary American.
Neighborhood: West Loop.
Vibe: This elegant yet understatedly designed fine-dining restaurant by Executive Chef and owner Noah Sandoval is one of the city’s hottest reservations. With two Michelin stars and flawless service, consider Oriole a special occasion splurge.
Best Dish: New Zealand langoustine with tapioca and melon in a warm coconut broth.
Unique Selling Point: Elevate your experience by booking a table at Oriole’s Kitchen Table and adding a night’s stay at the newly debuted Loft. The Loft is a furnished room with a king-sized bed, kitchenette, cookbooks, yoga mats, a full-sized drum kit, guitar, and amps. Oriole takes Chicago dining to exceptional levels.

Cuisine: Danish-influenced American cuisine.
West Loop.
Scandi-minimal meets convivial nordic hygge.
Best Dish:
Roasted lamb saddle with sunchokes, rhubarb, and Marcona almonds.
Unique Selling Point:
A show stopping set menu that can be paired with wine or juice means diners can place themselves in the competent hands of Executive Chef David Posey.

Cuisine: Contemporary American.
Neighborhood: Lincoln Park.
Vibe: Pushing boundaries of creativity with each meal, Alinea’s space is modern and convivial, attracting locals and jetsetters alike.
Best Dish: Potato Truffle Explosion—a decadent bite of ravioli filled with an intense truffle sauce.
Unique Selling Point: One of only 13 U.S. restaurants to receive three Michelin stars.

Cuisine: Modern Filipino restaurant and bakery.
East Ukrainian Village.
Vibe: Refreshingly low-key atmosphere known equally for brunch and dinner. Frequented by locals and often filled with lively and large family gatherings.
Best Dish: Longanisa sausage breakfast sandwich and buttery croissants.
Unique Selling Point:
The Fine Dining Filipino Inspired Tasting Menu is not to be missed at this James Beard Foundation Award Winner. Book 45 days in advance.

Pequod’s Pizza
Cuisine: Pizza (and pasta).
Lincoln Park.
Busy, busy, busy casual neighborhood sports bar.
Best Dish: Chicago’s best pan pizza. Choose personal, small, medium, or large size with toppings to satisfy everyone in your party.
Unique Selling Point:
Ships nationwide with Goldbelly.

What to do: Exploring Chicago Neighborhoods

Chicago has 77 designated community areas that makeup over 200 neighborhoods. Again with those numbers, Chicago! With so many unique areas to roam, visitors will watch their step counters rise to peak levels each day. Some of the best neighborhoods to wander during a weekend in Chicago follow.

The Loop is the beating heart of the city. Its name is said to derive from the cable cars that circled the city’s central business district in the late 1800s. This 35-block area of downtown Chicago is touristy, yes, but worth joining the crowds to see some of Chicago’s best attractions. Millennium Park, Cloud Gate (aka ‘The Bean’), and the Chicago Art Institute can all be found here. The Loop also has some of the city’s finest architecture including soaring skyscrapers like the 110-story Willis Tower (formerly the Sears Tower).

If the Loop is Chicago’s heart, then the West Loop is its stomach. Formerly an industrial area, its historic warehouses now house some of Chicago’s best restaurants. A foodie mecca, don’t miss the stretch of Randolph Street known as ‘Restaurant Row’. Whether hungry for house-smoked BBQ in a former meat-packing space, a little ramen joint, or a 4th generation sandwich shop, if you live to eat, the West Loop is for you.

Beyond food, the West Loop is also one of the best neighborhoods for entertainment and sports as it’s close to the United Center and theaters. Edgy, trendy, cool—pick your favorite adjective—you can’t make a wrong choice in the West Loop.

Logan Square is an artsy neighborhood with a super-chill, laid-back aura. One of the most ethnically diverse areas of the city, it’s bursting with trendy cafés, late-night bars, and hipster music venues. No wonder so many Chicagoans long to call this neighborhood home. The Logan Square Farmers Market runs each Sunday between May and October. It’s a great place to soak up the local vibe.

Head to brunch at farm-to-table pioneer, Lula Café (a Logan Square institution for over 20 years) for buttermilk pancakes or cannoli french toast. Play old-school pinball at Logan Arcade. Admire the eagle-topped Doric column of the Illinois Centennial Monument. Then round out your evening with a variety of taprooms, craft breweries, or high-end cocktail bars. No doubt there’s more to see and do in Logan Square than you’ll have time for.

Chicago’s Hyde Park is like a small town hidden in a big city. Blending big culture and small local businesses, this beautiful neighborhood is brimming with activities and sights, as well as some of Chicago’s best restaurants. Walk the University of Chicago’s campus. Take a stroll through the gardens of Midway Plaisance Park during the summer or ice skate in winter. Too cold to walk or skate, head to the Frederick C. Robie House or the Museum of Science and Industry to fire up your brain.

Lincoln Park’s wide green spaces and waterfront access make it one of Chi-Town’s most popular neighborhoods to explore, especially for nature lovers. Lincoln Park is home to Chicago’s famous (and free!) zoo which has over 200 animal species to observe as well as the Lincoln Park Conservatory where visitors can swoon over exotic flowers in four glass-covered display houses.

If shopping is more your speed, wander over to Armitage and Halsted for a dizzying array of boutiques. Don’t forget to try Chicago’s best pan pizza at Pequod’s after you are officially shopped out. Lincoln Park’s local, sociable feel, outdoor spaces, farmer’s markets, and numerous dining options make it a must-visit neighborhood year-round.

A Weekend in Chicago: Insider Tips and Local Knowledge

There’s nothing better than local knowledge. Thankfully the team at CIRE knows a thing or two about the Windy City. Whether you’re there for the weekend or decide to stay a bit longer, these insider tips will make visiting Chicago a breeze.

Buying a Chicago CityPASS will not only save you money (by up to 48%) on five Chicago attractions, but it will save you precious time on your weekend away. This all-access pass includes expedited entry to attractions like Skydeck Chicago and Shedd Aquarium. Add on three more activities of your choice like the Art Institute of Chicago, the Museum of Science and Industry, and the Shoreline Sightseeing Architecture River Tour. Skip the lines—having a CityPASS is the best way to explore Chicago.

Many Chicago attractions cost nothing at all. One of the best free sights is the Chicago Cultural Center where visitors can see the world’s largest glass Tiffany dome. Other Chicago freebies include the Lincoln Park Zoo and the world-famous Millennium Park, where the city’s most iconic piece of art resides. Cloud Gate (aka ‘The Bean’) is an ever-instagrammable spot. Check the calendar—tourists can also catch free movies and concerts here.

Need more ideas to round out your trip? Take the ‘El’ train, a Chicago must and an efficient way to get around town. Bike the beautiful lakefront. Dive headfirst into Chicago’s famous deep-dish pizza. Take a scenic river cruise. Explore lesser-known neighborhoods like Wicker Park and Andersonville.

Sample Paczki (deep-fried dough filled with a sweet filling) at a local bakery. Lay low at a speakeasy or laugh until you cry at a comedy club. Head to Cindy’s Rooftop at the Chicago Athletic Association Hotel for some of the best city views.

You’ve Got Our Number

Who better to help you plan your weekend in Chicago than the team at CIRE? From securing a coveted dinner reservation at one of the best restaurants in Chicago to booking a suite at a luxury hotel, CIRE is waiting on standby. The numbers don’t lie. There are hundreds of reasons to visit Chicago. Discover why millions of visitors flock to this fabulous city each year. And, get ready to be wowed.

CIRE Travel is a full-service travel agency headquartered in New York, NY.  Our expert corporate travel planners, honeymoon travel agents, and luxury travel planners support clients across the country and around the world.

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