Shannon O'Brien Travel Itineraries

The best destinations

Chicago skyline over the river
Chicago skyline over the river

The Best of Illinois

#29 best destination in the world

Map view

360 Chicago Observation Deck

Chicago, Illinois, USA - Aug 15, 2019: Tilting glass at John Hancock Center observation area

Best time to visit: April-May, Sept-Oct

  • 360 Chicago Observation Deck, formerly known as the John Hancock Observatory, is located on the 94th floor of the John Hancock Center in Chicago
  • It offers stunning 360-degree views of the city, including the skyline, Lake Michigan, and on clear days, visibility extends to four neighboring states
  • Visitors can enjoy interactive displays and exhibits, as well as a thrilling experience called TILT, which allows guests to lean out over the city

Art Institute of Chicago

Chicago, USA - June 05, 2018: Lion sculpture front of the Art Institute of Chicago.

Best time to visit: April-May, Sept-Oct

  • The Art Institute of Chicago, founded in 1879, is one of the oldest and largest art museums in the United States
  • Its collection includes works such as Georges Seurat's A Sunday on La Grande Jatte, Pablo Picasso's The Old Guitarist, Edward Hopper's Nighthawks, and Grant Wood's American Gothic
  • Its permanent collection of nearly 300,000 works of art is augmented by more than 30 special exhibitions mounted yearly that illuminate aspects of the collection and present curatorial and scientific research

Chicago Architecture Center

CHICAGO, IL -12 FEB 2018-  View of a large scale model of the modern Chicago skyline on display at the Chicago Architecture Foundation (CAF) building on Michigan Avenue in Chicago, Illinois.

Best time to visit: April-May, Sept-Oct

  • The Chicago Architecture Center is a nonprofit cultural organization based in Chicago, whose mission is to inspire people to discover why design matters
  • Founded in 1966, its programs include public tours and programs, most notably the docent-led architecture cruise on the Chicago River, and other tours in the Chicago area
  • In 2009, the center opened a new exhibition, Chicago Model, which includes a 3D-printed scale model of the central area of the city and is now on permanent display

Chicago River

Chicago skyline over the river

Best time to visit: April-May, Sept-Oct

  • The Chicago River is a system of rivers and canals with a combined length of 156 miles (251 km) that runs through the city of Chicago, including its center
  • The river is notable because it is one of the reasons for Chicago's geographic importance: it is a link between the Great Lakes and the Mississippi River Basin, and ultimately the Gulf of Mexico
  • The river is also noteworthy for its natural and human-engineered history
  • As part of a more than fifty-year-old Chicago tradition, the Chicago River is dyed green in observance of St. Patrick's Day (The actual event occurs on the Saturday on or before March 17)

Chicago Riverwalk

Chicago, IL - April 30 2024: People sitting, relaxing, strolling, reading at the steps next to the Chicago riverwalk with the setting sun reflected on the buildings in the distance

Best time to visit: April-May, Sept-Oct

  • The Chicago Riverwalk is a pedestrian-friendly waterfront space located along the banks of the Chicago River
  • Visitors can enjoy a variety of activities, including dining at restaurants, exploring public art installations, visiting museums, and taking part in water activities such as boat tours

Cloud Gate, Chicago

CHICAGO - MAY 18: Cloud Gate sculpture in Millenium park on May 18, 2013 in Chicago, IL. This public sculpture is the centerpiece of the AT&T Plaza in Millennium Park within the Loop community area.

Best time to visit: April-May, Sept-Oct

  • Cloud Gate, commonly known as The Bean, is a renowned public sculpture located in Millennium Park in Chicago
  • Constructed between 2004 and 2006, the sculpture is nicknamed "The Bean" because of its shape
  • It serves as a centerpiece of the park and has become one of Chicago's most iconic landmarks
  • Made up of 168 stainless steel plates welded together, its reflective and highly polished exterior has no visible seams
  • The design was inspired by liquid mercury and the sculpture's surface reflects and distorts the city's skyline and clouds moving overhead

Field Museum of Natural History, Chicago

Chicago, Illinois, United States, August 12, 2023  Field Museum of Natural History, looking down on lobby main floor,

Best time to visit: April-May, Sept-Oct

  • The Field Museum of Natural History, located in Chicago, is a museum dedicated to the study and exhibition of natural history and anthropology
  • Established in 1893, the museum houses approximately 24 million objects, including fossils, cultural artifacts, and specimens from various fields of natural history
  • Notably, it is home to SUE, the world's most complete Tyrannosaurus rex skeleton
  • Popular exhibits include the Ancient Americas, which showcases 13,000 years of human history in the western hemisphere

Millennium Park, Chicago

Chicago, Illinois 08-09-19 Crown Fountain video sculture by Jaume Plensa and reflection in Millennium Park on cloudless early summer morning.

Best time to visit: April-May, Sept-Oct

  • Millennium Park is a public park located in Chicago, opened in 2004
  • It is a prominent civic center near the city's Lake Michigan shoreline that covers a section of Grant Park
  • The park features a variety of public art, outdoor spaces and venues
  • Millennium Park has received awards for its accessibility and green design
  • Millennium Park has free admission, and features the Jay Pritzker Pavilion, Cloud Gate, the Crown Fountain, the Lurie Garden, and various other attractions
  • The park it is considered the world's largest rooftop garden

Museum of Science and Industry, Chicago

Museum of Science and Industry in Chicago

Best time to visit: April-May, Sept-Oct

  • The Griffin Museum of Science and Industry (formerly known as the Museum of Science and Industry), is a science museum located in Chicago
  • It opened in 1933 during the Century of Progress Exposition, and was renamed for benefactor and financier Kenneth C. Griffin in 2024
  • Among the museum's most notable exhibits are a full-size replica coal mine, German submarine U-505 captured during World War II, a United Airlines Boeing 727, the first streamlined diesel-powered passenger train in the US (Pioneer Zephyr), the command module of Apollo 8, and a 3,500-square-foot (330 m2) model railroad
  • Other exhibits cover manufacturing, environmental science, chemistry, physics, computers, the brain, and mechanics of the human body

CHICAGO -  AUGUST 26: Chicago´s number one tourist attraction, the Navy Pier, in Chicago on August 26, 2011. The Navy Pier is 3,300 ft long and built in 1916 at a cost of $4.5 million.

Best time to visit: April-May, Sept-Oct

  • Navy Pier is a 3,300-foot-long (1,010 m) pier on the shoreline of Lake Michigan, located in Chicago
  • The Pier encompasses shops, restaurants, live theaters, family attractions, parks, gardens, and exhibition facilities
  • Completed in 1916, it is one of the most visited attractions in the entire Midwest
  • It is also home to Offshore, recognized as the world's largest rooftop venue, providing panoramic views of the skyline and lake

Oak Street Beach, Chicago

Ohio Street Beach, Chicago

Best time to visit: April-May, Sept-Oct

  • Oak Street Beach is a popular urban beach located in Chicago, along the shore of Lake Michigan
  • The beach offers various amenities, including chair rentals, food and beverage options, and bike rentals
  • Despite being in a metropolitan area, Oak Street Beach is noted for its cleanliness and scenic views, with the Chicago skyline providing a striking backdrop
  • The beach has been a popular destination since the 1890s and has played a significant role in the development of Chicago's lakefront

Skydeck Chicago - Willis Tower

Three brave people on the glass platform on the skydeck of the  tower in Chicago, which gives the sensation of flying in the city view

Best time to visit: April-May, Sept-Oct

  • The Willis Tower Skydeck is an observation deck located on the 103rd floor of the Willis Tower (formerly known as the Sears Tower) in Chicago
  • It stands at 1,353 feet (412.4 meters) above ground, making it the highest observation deck in the United States
  • On clear days, visitors can see up to four states and 50 miles across the landscape
  • A notable feature of the Skydeck is "The Ledge," which consists of glass boxes that extend 4.3 feet out from the building, allowing visitors to experience the views while feeling suspended in the air

The Magnificent Mile, Chicago

May 14, 2013 - Chicago, Illinois: View along the Magnificent Mile in Chicago on a warm spring day.

Best time to visit: April-May, Sept-Oct

  • The Magnificent Mile is a section of Michigan Avenue in Chicago
  • It contains a mixture of upscale department stores, restaurants, luxury retailers, residential and commercial buildings, financial services companies, and hotels
  • The Magnificent Mile has many tall buildings and landmarks such as John Hancock, Wrigley Building, Tribune Tower, Chicago Water Tower, and the Allerton, Drake and Intercontinental Hotels

Wrigley Field, Chicago

CHICAGO, IL -- APRIL 30, 2010: The Chicago Cubs defeated the Arizona Diamondbacks during a Friday afternoon game at Wrigley Field on April 30, 2010 in Chicago, Illinois

Best time to visit: April-May, Sept-Oct

  • Wrigley Field is a ballpark in Chicago, and the home ballpark of Major League Baseball's Chicago Cubs
  • It first opened in 1914 as Weeghman Park for Charles Weeghman's Chicago Whales of the Federal League, which folded after the 1915 baseball season
  • The Cubs played their first home game at the park on April 20, 1916, defeating the Cincinnati Reds 7–6 in 11 innings
  • Chewing gum magnate William Wrigley Jr. of the Wrigley Company acquired the Cubs in 1921, where it was renamed Wrigley Field in 1927
  • The oldest park in the National League, it is the second-oldest in the majors after Fenway Park (1912), and the only remaining Federal League park
  • Wrigley Field's features include its ivy-covered brick outfield wall, distinctive wind patterns off Lake Michigan, the red marquee over the main entrance, and the hand-turned scoreboard

Garden of the Gods Observation Trail, Shawnee National Forest

Sunny Skies and Fall Colors in Garden of the Gods in Shawnee National Forest in Southern Illinois

Walk difficulty: easy

  • The Garden of the Gods Observation Trail is a scenic hiking loop located in the Shawnee National Forest
  • The trail offers panoramic views of the unique sandstone rock formations of the region and the Shawnee Hills
  • Hikers can see several iconic rock formations along the trail, such as Camel Rock, Table Rock, and Devil’s Smokestack