A Food-Lover’s Weekend in Chicago

Kat Bundy on March 25, 2026

3-Day Itineraries for Couples and Families Flying from TRI

Chicago is one of America’s most exciting food and cultural destinations. With world-class museums, scenic lakefront parks, and one of the most celebrated restaurant scenes in the United States, the city offers endless opportunities for a memorable weekend getaway. According to Choose Chicago, visitors come from around the world to experience Chicago’s architecture, cultural attractions, and legendary dining.

With nonstop flights from TRI to Chicago O’Hare International Airport, the Windy City is now a perfect long-weekend destination.

With a little help from AI, we’ve created two sample itineraries designed to help travelers experience Chicago: a romantic, food-focused weekend for couples and a fun, activity-packed family adventure.

Romantic Chicago Weekend for Couples

A culture and cuisine getaway

Chicago’s restaurant scene spans everything from Michelin-starred tasting menus to neighborhood institutions serving iconic local dishes.

Day 1: Iconic Chicago & West Loop Dining

Start your weekend at Millennium Park, home to the famous Cloud Gate sculpture (“The Bean”). After taking photos and enjoying the gardens, walk south through Grant Park for views of Lake Michigan. Next, explore the Chicago Riverwalk. Couples can grab a drink at a riverside café, take an architectural boat tour, or simply enjoy skyline views.

Dinner in the West Loop–Chicago’s trendiest dining district

  • Upscale: Girl & the Goat – One of Chicago’s most famous restaurants featuring globally inspired small plates.
  • Mid-range: Avec – Mediterranean small plates and wine in a cozy setting.
  • Casual: The Publican – Known for pork dishes, seafood, and craft beer.

Day 1 Total:

  • Activities: $0–$40
  • Dinner & drinks: $100–$150

Day 2: Museums, Architecture, & Michelin Dining

Begin the day at the world-renowned Art Institute of Chicago, one of the largest and most respected art museums in the world. Afterward, visit Navy Pier for lakefront views and a ride on the Centennial Wheel. Later, explore the historic Magnificent Mile for boutiques, cafes, and rooftop bars.

Dinner Options

  • Luxury: Alinea – A three-Michelin-star restaurant known for theatrical tasting menus.
  • Upscale: North Pond – Seasonal cuisine overlooking Lincoln Park.
  • Classic Chicago Steakhouse: Gene & Georgetti – A historic Italian steakhouse operating since 1941.

Day 2 Total:

  • Museum tickets: ~$60
  • Dinner: $120–$300

Day 3: Brunch, Neighborhoods & Lakefront Walks

Start the day exploring Lincoln Park and the free Lincoln Park Zoo. Walk along the Lake Michigan shoreline or rent bikes on the Lakefront Trail.

Brunch Options

  • Upscale Brunch: Boka – Michelin-starred modern American cuisine.
  • Popular Chicago Brunch: The Bongo Room – Famous for creative pancakes and brunch dishes.
  • Casual Café: Wildberry Pancakes & Cafe – A favorite for waffles and fresh pastries.

Day 3 Total:

  • Activities: Free
  • Brunch: $40–$70

Family-Friendly Chicago Weekend

A kid-approved city adventure

Chicago is packed with family attractions, interactive museums, and outdoor spaces perfect for kids.

Day 1: Parks, Fountains, & Pizza

Start at Millennium Park where kids love the interactive Crown Fountain. Then walk through Maggie Daley Park, a nearby space featuring playgrounds, climbing walls, and skating ribbons.

Dinner: Chicago Pizza Night

  • Classic Deep Dish – Lou Malnati’s Pizzeria
  • Stuffed Pizza – Giordano’s
  • Family-friendly Italian – Quartino Ristorante

Day 1 Total:

  • Activities: Free
  • Dinner: ~$70

Day 2: Aquarium & Museum Campus

Spend the day exploring Shedd Aquarium, home to thousands of aquatic animals. Next, visit nearby Field Museum, where kids can see Sue the T-Rex skeleton and hands-on exhibits. Finish the afternoon relaxing in Grant Park.

Lunch Options

  • Chicago Classic: Portillo’s – Hot dogs and Italian beef sandwiches.
  • Quick & Casual: Shake Shack – Burgers and milkshakes.
  • Local Favorite: Eleven City Diner – Large deli sandwiches and kid-friendly comfort food.

Day 2 Total:

  • Aquarium + museum tickets: ~$140
  • Lunch/snacks: ~$50

Day 3: Navy Pier & Lakefront Adventure

Spend the morning at Navy Pier where families can ride the Centennial Wheel, watch street performers, and explore lakeside parks. Take a walk along the Chicago Riverwalk before heading back to the airport.

Lunch & Treats

  • Kid-favorite burgers: Ed Debevic’s – A fun retro diner experience.
  • Sweet treat: Garrett Popcorn Shops – Famous Chicago caramel and cheese popcorn.

Day 3 Total:

  • Pier attractions: ~$50
  • Lunch & treats: ~$60
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Start Your Chicago Weekend at TRI

From Michelin-starred restaurants and deep-dish pizza to world-class museums and family-friendly parks, Chicago offers a weekend getaway packed with unforgettable experiences.

Book Now

Tri-Cities to Chicago Travel Guide: Discover the Windy City from TRI

Kat Bundy on March 25, 2026

Looking for an exciting city getaway with world-class attractions, incredible food, and unforgettable skyline views? Chicago, Illinois offers travelers an energetic blend of culture, history, and lakeside beauty, and getting there is easy when you begin your journey at Tri-Cities Airport.

With nonstop service to Chicago on both American Airlines and United Airlines beginning summer 2026, travelers can fly from Northeast Tennessee and Southwest Virginia to O’Hare International Airport, one of the world’s busiest and most connected airports. From there, visitors are just minutes from some of America’s most iconic attractions.

Must-See Chicago Attractions

One of the city’s most recognizable landmarks is Millennium Park, home to the famous Cloud Gate sculpture (often nicknamed “The Bean”). The park hosts concerts, public art installations, and beautiful green spaces that make it a favorite stop for visitors exploring downtown.

A short walk away sits Navy Pier, a vibrant waterfront destination along Lake Michigan featuring restaurants, boat cruises, family attractions, gardens, and stunning skyline views.

Travelers also love strolling along the scenic Chicago Riverwalk, where cafes, kayak rentals, and outdoor seating provide the perfect way to experience Chicago’s legendary architecture up close.

A City for Food Lovers

Chicago’s dining is as iconic as its skyline and its consistently ranked among the nation’s best cities for food-focused travelers.

Visitors often come to try classic local dishes like deep-dish pizza, Chicago-style hot dogs, and Italian beef sandwiches, but that’s not all the Windy City has to offer. The 2026 Michelin Guide recognizes 21 Chicago restaurants with star honors and 33 more with “Bib Gourmands,” the guide’s recognition for restaurants offering high-quality food for an incredible value.

Food lovers can explore diverse neighborhoods offering unique cultural dining or visit major culinary events such as the Taste of Chicago, one of the largest food festivals in the world.

Start Your Chicago Adventure at TRI

Whether you’re planning a long weekend getaway, a culinary adventure, or a cultural escape, Chicago offers something for every traveler. The city welcomes tens of millions of visitors annually thanks to its renowned museums, theater scene, lakefront parks, and vibrant neighborhoods.

Ready to explore the Windy City?

With new nonstop service on American Airlines and United Airlines, starting your trip at Tri-Cities Airport means less stress, short commute, and a smooth start to your journey.

Plan your trip today:

Your next great adventure might start closer to home than you think. ✈️

Tri-Cities Airport Announces New Daily Nonstop Service to Chicago O’Hare on American Airlines

Kylie Toler on December 18, 2025

Tri-Cities Airport (TRI) announced today that American Airlines will launch new daily nonstop service to Chicago O’Hare International Airport (ORD) beginning May 21, 2026. Tickets for the new route will go on sale Monday, December 22.

This new daily service gives travelers more flexibility and convenience when flying out of Tri-Cities Airport. With nonstop access to Chicago O’Hare, passengers can easily connect to hundreds of destinations across the U.S. and around the world.

“This is a significant addition for our airport and our region, one we’ve been working toward for a long time,” said Gene Cossey, President & CEO of Tri-Cities Airport. “We know there’s strong demand for this service, so we’re excited to finally be able to offer it to our local passengers. We’re proud to continue growing air service in ways that meet the needs of our community and support regional economic development.”

As a major hub for American Airlines, Chicago O’Hare connects travelers from Tri-Cities Airport to an extensive network of cities and markets. Its hub status ensures not only frequent flight options but also the support of a global airline network, making it easier to coordinate business or leisure travel anywhere in the country or beyond.

“We’re excited to introduce new nonstop service between Tri-Cities Airport and Chicago O’Hare, one of American’s largest hubs,” said Franco Tedeschi, Vice President of US Airports and Strategic Partnerships. “This route is designed to foster connections- whether meeting with business partners, visiting family, or exploring new destinations, customers in the Tri-Cities region will now have easier access to hundreds of cities across our global network, helping them stay connected to the people and places that matter most to them.”

Behind the new service is a strong, collaborative effort involving local businesses, regional partners, and community leaders. TRI was recently awarded $900,000 through the U.S. Department of Transportation’s Small Community Air Service Development (SCASD) Program, which helped support the launch of the Chicago O’Hare route. Input from local employers and stakeholders played a key role in identifying Chicago as a priority market that would deliver the greatest benefit to the region.

“We’re so grateful for the support that made this new route possible,” said Cossey. “We want to thank all the local businesses, leaders, and community partners that pledged their support, the Department of Transportation for awarding this grant, and of course American Airlines for seeing the value in our region and taking advantage of this great opportunity.”

The SCASD Program is designed to help small and mid-sized communities strengthen air service and improve access to the national air transportation system. TRI has worked over the past year to align federal resources with local support to grow sustainable air service that meets regional demand.

Daily nonstop service between Tri-Cities Airport and Chicago O’Hare will begin May 21, 2026. Flights can be booked starting December 22 at aa.com.

For more information about the new route and the SCASD Program:

Tri-Cities Airport is currently accepting donations for TSA employees. Drop off gift cards, food, & other everyday essentials at the Airport Services Counter.
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