Your web browser is out of date. Update your browser for more security, speed and the best experience on this site

Enjoying Illinois: Chicago and Galena

This short five-day trip will take you to some of Chicago’s top attractions with a quick detour to explore the quaint streets of Galena.

Navy Pier Fountain
Navy Pier, Chicago (Credit: Illinois Office of Tourism/Dick Sales)

Chicago is one of the United States’ great cities, offering visitors the chance to explore world-class museums, restaurants and entertainment. But Illinois is also home to a great example of small-town America: the charming town of Galena, located on the western edge of the state, just a short drive from the Mississippi River. This short five-day trip will take you to some of Chicago’s top attractions with a quick detour to explore the quaint streets of Galena.

Day 1 – Chicago

Morning: Fly into O’Hare International Airport

Afternoon: Walk and shop along Chicago’s famous Magnificent Mile

The Magnificent Mile is a 13-block stretch of Michigan Avenue in downtown Chicago that runs from the Chicago River north to Oak Street. The shopping and entertainment district—which stretches from both sides of Michigan Avenue, including east to Lake Michigan—contains more than 450 stores, 275 restaurants, 60 hotels and countless opportunities for exploration and excitement.

Evening: Visit 360 Chicago

Get an impressive view of the Windy City’s skyline at 360 Chicago, located on the 94th floor of the former John Hancock Building. Enjoy a 360-degree view of downtown Chicago, the famed Magnificent Mile, Lake Michigan and more. And don’t miss Tilt!, a new ride that extends out from the 94th floor, providing a unique view from more than 1,000 (300m) feet up.

Other ideas: Explore the newly renovated Chicago Riverwalk, which follows the Chicago River through downtown and offers users opportunities for recreation, public art exhibitions and more. Get a taste of true Chicago at Giordano’s, home to the city’s famous deep-dish pizza.

Day 2 – Chicago

Morning: Visit the Art Institute of Chicago

No visit to Chicago is complete without a visit to the Art Institute of Chicago, one of the oldest and largest art museums in the United States. There, you’ll see iconic works like Grant Wood’s “American Gothic” and Edward Hopper’s “Nighthawks”, as well as an extensive collection of historic and contemporary art from across the globe. The Art Institute is home to greatest collection of Impressionist paintings outside Paris, including works by Monet, Renoir, Seurat and van Gogh. Explore the Modern Wing and its extraordinary collection of works by Chagall, Dali, Matisse, Picasso and Pollack.

Afternoon: Explore Millennium Park

A lively gathering spot in the heart of downtown Chicago, Millennium Park hosts events throughout the year, including concerts, festivals and more. Be sure to take your picture by the famous “Cloud Gate” (also known as “The Bean”).

Evening: Catch a concert at The House of Blues

Music lovers: Don’t miss your opportunity to take in a live show at Chicago’s House of Blues, one of only a dozen House of Blues restaurants/performance venues in the United States. This Southern-inspired spot welcomes musical acts of all kinds, from hip-hop to country to (of course) blues. If you happen to be in town on a Sunday morning, don’t miss the House of Blues’ world-famous gospel brunch.

Other options: In the warmer months, visitors to Chicago can hop on board at Shoreline Sightseeing river tour to learn about the city’s history and iconic architecture. Learn about natural history at The Field Museum, home to “Sue,” the most complete and best-preserved Tyrannosaurus rex fossil yet discovered.

Day 3 – Chicago to Galena

Morning: Drive to Galena, Illinois (160 miles/260km, 3 hours)

Afternoon: Visit downtown Galena’s shops and galleries

Often voted as one of the best small towns in the United States, Galena is rich with history and charm. The city is home to many well-preserved 19th century homes—including the historic home of President Ulysses S. Grant—and Main Street in downtown Galena is lined with more than 100 storefronts—souvenir shops, antique stores, boutiques and more.

Evening: Dine at a downtown Galena restaurant

Galena offers an eclectic mix of cuisines, from classic American steakhouses to high-end Italian eateries. And, best of all, many of the area’s most popular restaurants are located in Galena’s historic downtown. For a true supper club experience, visit Log Cabin Steakhouse, which has been serving customers for 80 years. Find traditional Italian dishes at Fried Green Tomatoes or Vinny Vannuchi’s.

Other options: If you’re feeling adventurous, spend a few hours with Longhollow Canopy Tours, which takes visitors on a zipline tour of the scenic Galena countryside. Learn about small-batch spirits with a tour and tasting at Blaum Bros. Distilling.

Day 4 – Galena to Chicago

Morning: Take in views of the Mississippi River at Chestnut Mountain Resort

Sitting along the banks of the Mississippi River, Chestnut Mountain Resort is one of the top year-round resorts in the Midwest. Visitors will discover fun activities like ziplining and an alpine slide in the summer and scenic skiing and snowboarding in the winter. Plus, boat tours of the Mississippi River are available in the spring, summer and fall.

Afternoon: Drive to Chicago, Illinois (160 miles/260km, 3 hours)

Evening: Dine, shop and discover attractions at Navy Pier

Navy Pier, which extends into Lake Michigan along Chicago’s lakefront, has long been a popular attraction for visitors. The landmark building, which is open year-round, boasts countless events, as well as options for shopping and dining, as well as the famous Centennial Wheel.

Other options: See examples of world-renowned architect Frank Lloyd Wright’s iconic style at locations throughout the Chicago area, including the Emil Bach House and the suburb of Oak Park, which is home to Wright’s home and studio. Head to Buddy Guy’s Legends for some great live music with a side of soul food.

Day 5 – Chicago

Morning: Depart from Chicago O’Hare International Airport