Choose Chicago and American Airlines asked three Chicago locals to invite an out-of-town friend for a personalized weekend in the city. Check out their itineraries and enter for a chance to win a trip to Chicago.

 See the weekends
Influencer Andy Lamb
Influencer Kat Dunn

Urban Hot Spots

Influencer Eddie Zamora
Influencer Steve Green


Influencer Taylor Fuller
Influencer Silvana Favaretto

Eclectic Outings

Kat and Any at Navy Pier


Influencer Andy Lamn

Andy Lamb |

Chicago resident and avid traveler, Andy is the go-to guru for all the latest happenings.

Influencer Kat Dunn

Kathryn Dunn |

Currently a Dallas-based TV host and blogger, formerly an NBA dancer and pageant queen.

Meet Andy & Kat

The party goes wherever Kat Dunn and Andy Lamb go, so we made them an itinerary to match. Their weekend is all about what’s trending throughout the city, from the latest hot spots to the coolest shows and events.

Want to recreate their weekend? With this action-packed itinerary, you’ll paddle along the Chicago River, soar 103 floors above the city, party in Boystown and get a taste of some of the buzziest bites and sips in the city.

Andy & Kat's Itinerary

Kat and Andy at the Moxy Hotel

First up, the duo checked in to one of River North’s newest hotels. These trendy digs are the perfect spot to stay and play in one of Chicago’s liveliest areas, brimming with nightclubs, decadent restaurants, art galleries and more.

Pool area at Aire Baths Chicago

Kat and Andy kicked off their jam-packed weekend with a morning of total zen. Located in a restored factory from 1902, AIRE is an unforgettable experience inspired by the ancient tradition of thermal baths. The pair blissed out in the soothing pools, while soaking in the splendor of the exposed brick and soaring wooden beams of the industrial-era building.

Various Desert food from Flight Club Chicago

This downtown spot takes shooting darts to a whole new level. Flight Club offers fast-paced multiplayer games, alongside bespoke cocktails and shareable food options.

Kat and Andy snacked on meatball sliders and a chocolate dessert flight as they tried their hand at a few rounds of darts – and sipped on a cocktail or two. Afterward, they headed out to the nearby Riverwalk and over to Michigan Avenue for some shopping.

Escape room puzzle on Escape Artistry Chicago

Now that they’ve flexed their throwing arm, it’s time to give their minds a workout. Kat and Andy were up for the challenge, taking on The Railcar room escape. In this interactive adventure game, the two searched for clues, solved puzzles and cracked codes in order to escape from one of the city’s iconic L train cars.

Drinking at Navy Pier

After a quick pit stop at Moxy, the pair were ready to set sail on the Spirit of Chicago. The dinner cruise departs from Navy Pier and offers stunning views of the skyline from Lake Michigan.

During their swanky evening on the water, Kat and Andy danced to an onboard DJ, visited the extensive buffet and sipped on creative cocktails from the cash bar.

Influncers posing aboive Chicago skyscrappers at SkyDeck

Chicago’s Skydeck, the highest observatory in the Western Hemisphere, is perched on the 103rd story of the Willis Tower. Kat and Andy checked out the sweeping views spanning up to 50 miles and interactive exhibits highlighting the area’s history. They even braved The Ledge, a set of glass balconies that hover 1,353 feet above the city, to catch a glimpse of the best Chicago sights – and snap a few selfies, of course.

Pizza and other food from Brunch Bar Siena

Tucked along the West Loop’s trendy Restaurant Row, Bar Siena is inspired by classic Italian street food. It’s a popular spot for brunch, when diners can dig into from-scratch dishes served cicchetti-style – intended to be shared. Kat and Andy took full advantage of this, splitting a breakfast pizza, avocado toast, and cherry almond granola.

Kayak on chicago River from Urban Kayaks

Kat and Andy are all about making a splash. The two had a blast exploring the heart of downtown on the Chicago River. They paddled along in the shadow of some of the city’s most famous buildings, admiring the breathtaking architecture, soaking up the sun -- and only getting a little lost.

Influencers drinking at Dinner at Beatnik

After an active day, Kat and Andy stopped to relax and refuel at Beatnik. This buzzing West Town spot is an Instagrammers dream, full of lush plants and opulent, bohemian-inspired design. The menu spans the globe and pulls culinary inspiration from Mediterranean, Asian and Latin American countries.

Blue Man Group program pamphlet

The friends ended the night with a bang at The Blue Man Group. This mesmerizing spectacle combines color, music and art for a truly one-of-a-kind show. Andy and Kat got to experience the immersive performance first hand, including a meet-and-greet with the Blue Men themselves after the show.

Influeners pose outside of Wood

It’s not a Sunday in Chicago without brunch. Kat and Andy snagged a patio seat at Wood, a stylish spot in the heart of Boystown. With a creative menu composed of locally sourced ingredients, Wood has won the hearts of locals and critics alike. And it’s got plenty of accolades to prove it, including five Michelin Bib Gourmands.

Participants in rainbow colored outfits at Chicago Pride

What better way to end the weekend than with Chicago’s biggest party? Kat and Andy joined the 750,000 spectators who line the streets each year for the world-famous Chicago Pride Parade to celebrate the city’s LGBTQ community. The parade route travels four miles through the Uptown and Lakeview neighborhoods, getting especially exuberant in Boystown. Stake out a spot early, or pop in to the bars and restaurants joining the fun along the route.

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Influencers take selfies at Wrigley Field

Foodie Faves

Steve & Eddie's Itinerary

Elegant room at Hotel Zachary

Steve and Eddie met up at Hotel Zachary, directly across the street from historic Wrigley Field. With a variety of cuisine and cocktail options, including a popular taco joint, barbecue spot, American brasserie and more, the new hotel is the perfect starting point for this food-focused weekend.

Burger with egg and bacon from Mordecai in Chicago

This bi-level bar and restaurant inside Hotel Zachary has a full menu of refined, American-inspired fare. But the true emphasis is on the beverages. Steve and Eddie sipped on creative cocktails and limited-edition pours in the shadow of the ballpark before heading out to explore the Wrigleyville neighborhood.

Food from Three Dots and a Dash

Steve and Eddie kept the party going at this underground tiki bar, a rum-soaked oasis hidden below the lively streets of River North. They perused the menu of tropical-inspired drinks and appetizers, opting for various bites and one of the large-format cocktails to share.

Wine glass from The Milk Room

Once a Chicago speakeasy used during Prohibition, Milk Room’s eight-seat microbar is tucked away inside the Chicago Athletic Association. Steve and Eddie sampled from the curated selection of rare and vintage spirits, while soaking in the spot’s rich history.

Food and burrito from Green City Farmers Market

Steve and Eddie wandered through rows of farm-fresh fruits and veggies, baked goods, flowers, grass-fed meats and more at the Green City Farmers Market. The year-round market, the first and largest in Chicago, brings sustainably grown food from local farmers and producers straight to the community.

A pancake, bacon and eggs breakfast from Smoke Daddy

When it comes to brunch, Chicagoans tend to agree that bottomless is best. Steve and Eddie went for the family-style brunch at Smoke Daddy, a barbecue joint serving up classic smoked meats and more inside Hotel Zachary. Don’t forget to add on the never-ending mimosas and bloody marys to round out the meal.

Influencers pose for selfies in Chicago Cubs gear

The Friendly Confines is the second-oldest ballpark in the major leagues, famous for its ivy-lined outfield, human-operated scoreboard and the bleacher bums rallying the team to victory. Steve and Eddie cheered on the 2016 World Series Champions and ordered up ballpark classics, like nachos in a helmet and Chicago-style hot dogs (no ketchup, of course).

Cups a bear labeld with Chicago Cubs logo

The Cubby Bear is the fan favorite for Cubs pre- and post-game parties. Steve and Eddie celebrated a Cubs W at this classic corner bar with plenty of cold beer and live music.

Curbside of Hotel Versey

Steve and Eddie stayed at the newly revamped Hotel Versey on the edge of the Lakeview and Lincoln Park neighborhoods. The hotel prides itself on connecting visitors with the local culture, music, art and food and was featured in Architectural Digest's list of “12 Best Designed Hotels Opening This Year."

Various art prints from Old Town Art Fair

Time for a little culture. For more than 70 years, the Old Town Art Fair has brought exhibits from more than 250 artists to the streets of Old Town. Nearby, the newer Wells Street Art Festival boasts an eclectic array of art along the main stretch of the neighborhood. Steve and Eddie checked out the art while listening to the diverse lineup of live musical acts.

Menu from Chicago Beer Experience

Learning about Chicago history while sipping on craft brews? Sign us up. Steve and Eddie took the Pioneers & Pints Beer Tour through the Wicker Park and Bucktown neighborhoods, which pops into neighborhood bars and covers local history relating to immigration, pioneers, and (obviously) beer.

Irresistable desert pire from Bellemore

At Bellemore, the interior is just as stunning as the carefully composed plates. To celebrate the weekend, Steve and Eddie treated themselves to an array of decadent dishes, like the oyster and caviar pie. The West Loop restaurant is helmed by Jimmy Papadopoulos, one of Chicago’s most acclaimed chefs.

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Influencer Steve Green

Steve Green |

Founder of #FoodieChats. Steve now lives in Miami, but he’s a born-and-raised Chicagoan.

Influencer Eddie Zamora

Eddie Zamora |

LA-based writer, TV personality and photographer obsessed with all things food, wine and travel.


Foodie friends Steve Green and Eddie Zamora are ready for anything—especially when it involves great food, strong drinks and a chance to experience something new.

If you’re looking to get a taste of different parts of the city, this itinerary will be the perfect gourmet getaway. From a Chicago dog at the ballpark to a neighborhood beer tour to an extravagant dinner, Steve and Eddie’s weekend captures what food enthusiasts love about Chicago.

People observe paintings at The Art Institute of Chicago


Influencer Taylor Fuller

Taylor Fuller |

A full-time travel blogger and first-time Chicago visitor. New York raised, living in London.

Influencer Silvana Favaretto

Silvana Favaretto |

A fashion entrepreneur focused on female empowerment. Chicago-based with roots in Brazil.

Meet Taylor & Silvana

Taylor Fuller and Silvana Favaretto may seem like an unlikely duo. While Taylor would rather spend a low-key afternoon in a local taproom, Silvana is ready for a tulle skirt and rooftop cocktails. Fortunately, there’s something for everyone in Chicago.

This itinerary introduces a variety of Chicago’s neighborhoods and the unique eats and activities they have to offer. In just three days, you’ll get a glimpse of some of the city’s most diverse experiences.

Taylor & Silvana's Itinerary

Woman gazes out of window from Staypineapple The Loop Chicago, An Iconic Hotel

Taylor and Silvana met up at their homebase for the weekend in the Loop neighborhood. This boutique hotel is in a prime location near Millennium Park, the theatre district, top-notch dining and more. The pair spent the morning exploring the park and the rest of the Loop.

Chinese architecture in Chinatown

Taylor and Silvana dove into the weekend with a walking tour of Chinatown’s best bites. The food-focused tour includes five sit-down tastings from different regions of China, as an experienced guide explains Chinese culture and customs.

Influencers take selfie with headsets aboard Chicago Helicopter Experience

One of the best ways to see Chicago? From the sky. Taylor and Silvana took in panoramic views of the skyline and lakefront as they soared across the city on a helicopter tour. The exhilarating ride offers a once-in-a-lifetime perspective of all the major sites, from the Willis Tower to Navy Pier to Grant Park and more.

Food platters from Nana Chicago

The menu at Nana draws on a variety of cultures, from American to Spanish, making it an ideal stop for Taylor and Silvana’s eclectic weekend. The family-owned restaurant is beloved for its organic options made with local ingredients. The approachable menu is seasonal, sustainable, and most importantly, delicious.

Chicago is home to more than 65 breweries, and Chicago Friday Night Flights might just be the best way to sample as many as you can. The series of tasting events is held in a different neighborhood each time. Taylor and Silvana got to hit the beach, sipping samples of different local brews and enjoying the food vendors and live music.

View of Chicago lake from 360 Chicago

From the 360 CHICAGO observation deck, Taylor and Silvana got sweeping views of downtown Chicago and Lake Michigan. Perched 94 floors above the city, the observation deck is also home to Chicago’s highest thrill ride. TILT is a first-of-its-kind experience where visitors can hover above Michigan Avenue from more than 1,000 feet in the air.

Meat and eggs meal from River Roast Chicago

After seeing the city from above, it was time to get up close and personal. River Roast sits along the Chicago River and each seat offers a stunning view of the bustling waterway. A contemporary take on an American tavern, the spot’s menu features hand-carved meats, tasty veggie dishes and inventive drinks.

Influener poses along chicago River aboard Chicago's First Lady

The Chicago River weaves through the heart of the city, making it the perfect route to marvel at the city’s most iconic buildings. Taylor and Silvana got an in-depth tour of Chicago’s legendary architecture aboard Chicago’s First Lady. Highly trained guides provide a detailed narrative of the various architectural styles and the people who built them.

Cake-topped shake from Public House

Public House is known for two things: it’s upscale bar food and an impressive beer selection. Taylor and Silvana enjoyed both as they looked out over the buzzing streets of River North. They took advantage of the extensive drink menu, including rotating local drafts and craft cocktails, and the American smokehouse fare.

Black and white image of people riding Centennial Wheel

Navy Pier is Chicago’s lakefront gem. Taylor and Silvana explored the waterfront landmark, including a ride on the famous Centennial Wheel for 360-degree view of the city and lake. Plus, on Wednesdays and Saturdays throughout the summer, visitors can enjoy a free, spectacular fireworks show.

Long exposure of chicago roads at night from LondonHouse Rooftop

For a nightcap, the friends headed to the rooftop bar atop the LondonHouse Chicago hotel. The chic three-level space offers an unrivaled panorama of the Chicago River and the Magnificent Mile. As an added bonus, the spot serves beautifully crafted cocktails to match the stunning views.

Taco from La Bodega

To start the day, Taylor and Silvana visited a Mexican-inspired market with a twist. The walk-up counter in River North serves up a tempting array of sweet and savory items, from breakfast tacos to churros topped with sugary cereals.

People observe painting in The Art Institute of Chicago

No weekend in Chicago is complete without a stop at one of the world class museums. Taylor and Silvana opted for the Art Institute. One of the oldest museums in the country, the Art Institute is home to the largest collection of Impressionist and Post-Impressionist art outside the Louvre. The duo spent time checking out some of the most famous pieces, like American Gothic and Van Gogh’s self portrait.

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