Chicago vs Dallas

When these two cities go big, they go really big. From a larger than life football stadium, to competing Michelin star restaurants– these two cities share more than a skyline of striking architecture, passionate sports fans and a foodie following.

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The distinctive neighborhoods that make up these geographically big cities feature sky-stretching high-rise buildings, 19th century rowhouses, and modern art districts.

A Walk in the Park

Spend the day outside in these two park districts and take in modern marvels set against the great outdoors.

Chicago: Named the #1 tourist attraction in the Midwest, Millennium Park is located in Chicago’s famed Loop neighborhood and is just steps from Lake Michigan’s shoreline. You’ll head there for the famous reflective bean sculpture, but stay for a free show at the Frank Gehry designed Jay Pritzker Pavilion and a stroll along the stunning serpentine bridge.


Dallas: Among the garden grounds of the Dallas Arts District, is the breath-taking Nasher Sculpture Center featuring over 300 masterpieces that rotate throughout seasons. Flanking this impressive Garden is the museum designed by renowned architect, Renzo Piano. In all, this one-of-a-kind museum and garden take up a full city block.

Head in the Clouds

For sweeping city views and a 360-degree perspective take the express elevator up to these iconic towers.

Chicago: You may know it as the Sears Tower. Now called Willis Tower, it once boasted the title of the tallest building in the Western Hemisphere. Visit the infamous Sky Deck 103 floors up for unparalleled views of the city. Not for the faint of heart, the newest addition, simply called “The Ledge” is a 4-foot extension from the building encased in glass.

Dallas: A visit to Dallas means a visit to the landmark Reunion Tower for panoramic views of the Big D. From afar, this iconic tower looks like a glowing disco ball. Inside, the GeO-Deck provides a perch 450 feet high with both indoor and outdoor observation areas. Before you leave, head to Wolfgang Puck’s revolving restaurant, Five Sixty, with floor to ceiling windows and great cocktails.


These two cities host some of the most celebrated restaurants in the country. From molecular gastronomy, to homegrown classics, a visit to Dallas and Chicago means good eats from great chefs, old and new.

Head of the Class

Boasting Michelin star and James Beard winner accolades, these visionary restaurants are worth the price tag.

Chicago: Consistently celebrated as one of the best restaurants in the country and one of only 12 restaurants in the US with three Michelin stars, Alinea is one of those once-in-a-lifetime meals that is more of an experience than it is a meal. The edible helium balloon (yes, it really floats) is just one of the innovative science-experiment-like courses you’ll delight in.

Dallas: The newest venture from James Beard Award-winning Chef Stephan Pyles, is Flora Street Cafe in the Dallas Arts District. Snag a seat at the coveted chef’s counter for a visually stunning meal that shines by dabbling in molecular gastronomy.

Fast Food

Don’t worry, we’re not talking about chain restaurants. Try one of these fast, casual eateries serving the best regional cuisine in each city.

Chicago: Chicagoans take their hot dogs very seriously and so should you. Visit the Redhot Ranch for a double Depression Dog – the minimalist version of the Chicago-style loaded dog with snap. And please, we beg you, don’t ask for ketchup.

Dallas: Avila’s has been a Tex-Mex staple in Dallas for the last 25 years. A true marriage of Texan and Mexican decent, Avila’s owners have stayed true to classic family recipes, while creating new ones. Order their house specialty, the chile relleno, stuffed with tender shredded brisket and blanketed with melted cheese.

Home-grown Favorites

You can’t visit these two cities without trying the regional cuisines they are best known for.

Chicago: Don’t worry, we didn’t forget about a Chicago favorite – deep-dish pizza. Lou Malnati’s is a Chicago institution and home to the Chicago-style deep dish. With 31 locations in and around Chicago, there’s no excuse not to stumble upon a Lou’s quintessential pie made with a thick and tangy sauce and a crumbly buttercrust.

Dallas: The Slow Bone in the Dallas Design District offers some of the best bbq in town. The smoked, thick-crusted brisket and cafeteria-style sides, like the jalapeño mac and cheese are as good as it gets. But the star? It’s the fried chicken that’s infused with their famous smoke flavor.



From huge department stores to luxury stores and uniquely curated boutiques, these two cities set the standard when it comes to shopping.

Bigger IS better

Whether you’re window-shopping or stocking up on everything from beauty products to home goods, these luxury shopping retailers are the perfect one-stop shop.

Chicago: Magnificent Mile is an eight block stretch of downtown North Michigan Avenue full of luxury and high-fashion retailers. You won’t know where to start with the endless rows of luxury boutiques, malls full of brand name retailers, and department stores all within this short stretch.


Dallas: You may have visited plenty of Neiman Marcus’ locations in your time, but the prestigious Flagship department store is the crown jewel of the Main Street District in Dallas. Spectacular in service, and with an array of designers that can’t be found in other Neiman Marcus stores, this is a must-stop on your shopping tour.

Let Your Feet do the Talking

Put some pep in your step by slipping on one-of-a-kind footwear.

Chicago: Visit one of Bucketfeet’s three Chicago locations for some of the coolest and unique kicks in town. This store specializes in artist-designed footwear. Each pair is designed by one of the 40,000 artists the brand collaborates with from around the world.

Dallas: Technically this boot-making institution is just outside of Dallas in the Forth Worth neighborhood – but trust us when we say this is well worth the drive. M.L. Leddy’s is considered the Rolls Royce of Texas boots with a distinctive made-to-measure process and exotic skin selection.

Small Shops, Big Personality

These charming boutiques are a breath of fresh air with unique novelties full of personality.

Chicago: Located in Chicago’s Logan Square neighborhood, Tusk’s minimalist design and curated selection of vintage and contemporary clothing and accessories is ever evolving. The boutique also carries books, prints and objects and best of all, taps into local designers for locally-made goods.
Pro tip: Visit some of Chicago’s other cool neighborhoods like Lincoln Park, Southport Corridor, Old Town, and Wicker Park for more unique boutiques and curated shops.

Dallas: The Reese Witherspoon founded boutique, Draper James, embodies the style and charm of the South. Located in Highland Park Village, this chic storefront carries beautiful unique clothing creations as well as home goods and accessories.


From cool pictures to a rowdy sports scene, there are a few iconic places that stand out on their own and are special to these two cities.


Fans from Chicago and Dallas go head-to-head when it comes to unique sports venues and fans that live and breathe their home-state teams.

Chicago: Wrigley Field, on the North side of Chicago, is a 103-year old stadium institution and home to the beloved 2016 World Series Champions. Just in time for the 2017 season, the ballpark has undergone a major restoration and expansion, while still preserving the charm and historic features it’s known for including. an ivy-covered outfield wall, surrounding rooftop seats, and signature marquee. Take the L early and grab a few beers at the surrounding taverns almost as famous as the stadium itself.

Dallas: AT&T Stadium, home of the Dallas Cowboys, is young in age, but already regarded as one of the top stadiums in the league. With a die-hard fan base, signature cheerleaders, one of the largest LED screens in the world, and unparalleled pre-game entertainment, it’s no wonder the Cowboys are considered “America’s team”.

Grammable Moment

Both cities have that one must-take-a-picture spectacle. Keep your phone charged and start thinking about a creative pose.

Chicago: Kick off your trip with a visit to the Greetings From mural in Logan Square. A collaboration between graffiti artist Victor Ving and photographer Lisa Beggs, this piece pays homage to the vacation postcards from the mid-20th century.

Dallas: The giant eyeball sculpture on Dallas’s Main Street may be a bit of an enigma, but we won’t complain. This incredibly unique, and cool, piece of art was made by Artist Tony Tasset and sits at a staggering 30 feet high. Let the eye jokes commence.


Get Outside

From strolls along the river to a hip new green space, get outside and enjoy the best of these sprawling cities.

Chicago: It famously turns green on St. Patrick’s day and after a recent build of continuous pedestrian walkways, the Chicago Riverfront has become a bustling hub of activity 365 days a year. Visitors can stop at one of the many waterfront cafes and restaurants, rent boats, take in live musical performances, and enjoy one of the many special events rotating on the city’s calendar.


Dallas: In the heart of downtown Dallas is an urban green space, Klyde Warren Park. The park has become the city’s prime gathering space and offers a constantly diverse schedule of special events and programming. From outdoor yoga classes, to concerts, public gaming areas, and a beautiful dog park – the park has something for everyone to get outside and stay outside.

These big cities have no shortage of spectacular sites and distinctive high-rises as far as you can see. From the Windy City to the Big D, no matter where you visit, you go big or you go home. Literally.

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