2-Day City Sightseeing

2-Day City Sightseeing Trip Chicago

Day 1 You’ll See: 

Day 2 You’ll See:

Not everybody has all the time they would like to to see the Windy City, which is why we have created a small, easy, and extremely fun taste of Chicago for your group that we like to call the 2-Day City Sampler. On this weekend getaway your group will be able to explore the most fun, entertaining, and educational city hotspots while taking in that iconic city skyline and urban hustle and bustle these lakeside inhabitants are used to!

Explore some of the finest and most rare of their kind museums, aquariums, and parks, as well as some of the city’s most iconic buildings, towers, and landmark hot spots. Your group will have the chance to see the city from the sky at Willis Tower and from the water aboard an Architecture Foundation Cruise. You will eat at some of the most fun Chicago city spots, and be entertained by some of the most fun spots in the Windy City!




National Museum of Mexican Art - Start your trip off with this highly unique and educational experience at the National Museum of Mexican Art. Here your group will see over 3,000 years of creativity spanning through an impressive 7,500 piece permanent collection which upholds the highest museum standards.

  • Tienda Tzintzuntzan - Translating to Place of the Hummingbirds, this souvenir shop provides an eclectic variety of unique gifts, textiles, jewelry, books and toys!

Shedd Aquarium - Next stop, the Shedd Aquarium! Here your group will see over 32,000 animals, award-winning exhibits, and in-depth hands-on activities in this diverse, global animal collection that is surrounded by eye-popping architecture. Enjoy the stately marble building as well as all the opportunities to learn about, touch, and see amazing aquatic animals!

  • Caribbean Reef - Enjoy a 360 degree tour of an authentic reef community as you stroll around this 90,000 gallon tank full of green sea turtles, moray eels, rays, and shark.
  • Rice Amphitheater - Prepare for an exciting splashdown of 4D fun as you take in any of the current, mind-blowing 4D shows in this immersive amphitheater.

Grant Park- Spend your afternoon exploring ‘Chicago’s Front Yard’, the 319-acre central business district that includes Museum Campus, Millennium Park, Buckingham Fountain, the Art Institute, and several performance venues, gardens, art work, sporting events, and harbor facilities. There is something interesting to see in every direction in Grant Park!

  • Buckingham Fountain - Built in 1927 to protect lakefront views, this monumental city focal point is actually one of the world’s largest rococo style fountains, complete with a 20 minute nightly water and light display.
  • Festivals - This space is highly popular for it’s participation in annual music and event festivals, such as Lollapalooza, presidential inaugurations, and sporting championships.

Millennium Park  -Millennium Park is located within Grant Park and will provide a chicago_bean_nightgorgeous location to stroll around the state-of-the-art collection of architecture, landscape design, and outdoor art. This area is also the focus of hundreds of free cultural events annually.

  • The Bean - Officially named Cloud Gate, this iconic city landmark provides a new perspective to take that iconic city skyline photo or selfie in, with it’s famous mirror-like surface!
  • Lurie Gardens - Enjoy a break from the hustle and bustle as you look at all the perennial plants, hardwood bridges, and shallow show pools within this 5-acre botanic garden.

Willis Tower - Nothing can beat the views of Chicago from the sky, especially at night, as your group is about to learn at the Willis Tower. Also called Skydeck, this impressive cut in the city skyline is actually the tallest building in the entire Western Hemisphere, giving unbeatable views of 50 miles in the distance, reaching over 4 states of visibility on good days!

  • The Ledge - Step 4.3 feet out into the 1.353 foot tall drop below, with a glass encasement being the only barrier between the ground and yourself. Enjoy the thrilling view and don’t look down if you’re afraid of heights!



CHICAGO, IL - OCT 1: Navy Pier and skyline on October 1, 2013 in Chicago, Illinois. It was built in 1916 as 3300 foot pier for tour and excursion boats and is Chicago's number one tourist attraction.


Rock-n-Roll McDonald's - Enjoy some warm, classic McDonald’s breakfast at this rare, unique, and extremely fun central Chicago, River North rocking location. Enjoy the impressive collection of 50’s and 60’s memorabilia in one of the world’s most famous, and at one point busiest, McDonald’s establishment.

  • Upstairs Museum - Go explore the actual museum collection upstairs after eating, complete with the Elvis Presley cover of Time, plaster cast of the Beatles, and an authentic 1958 Corvette!

Wrigley Field - Welcome to the home of the Chicago Cubs, Wrigley Field. Here your group will see behind the scenes of the iconic field that has played host to major league baseball for over 101 seasons! Take any of the many offered daily tours, catch a game, or watch the players practice in season while you’re here!

  • Friendly Confines Tour- This 1.5 hour tour will take you to all the best spots on the field, including the press box, cubs clubhouse, dugout, field, and Jack Daniels Patio!
  • Cubs Game - If you happen to be here on a game day get ready to catch all the action with either pre-game practices or full on high-energy Cubs pitching and batting!

Navy Pier IMAX - The Navy Pier is the #1 leisure destination in the Midwest and will offer your group some of the best natural lakeside beauty and urban city skyline beauty. You will also have the chance to watch any of the latest blockbusters or scientific specials at their very own highly impressive, and immersive, IMAX Theater.

  • Dining - Choose from many of the diverse dining options on the pier before or after the show, ranging from the cinematically popular Bubba Gump’s Shrimp Co to McDonalds.
  • Navy Pier Park - Before or after your movie presentation let loose at Navy Pier Park, the place where your group can ride the iconic Ferris Wheel, take a spin on the Wave Swinger, or play a round of mini-golf!

Architecture Exchange Cruise - Get ready for one of the most unique and gorgeous chicago-673558_1280ways to see the city, also agreed to be one of the absolute ‘best ways to see Chicago’, aboard the Chicago First Lady Cruises. Enjoy all of the interesting information about architecture and about the design of over 50 iconic buildings along the Lake Michigan Shoreline!

  • Location - Find this stop by the blue awning at the Southeast corner of the Michigan Avenue Bridge, right off of Wacker Drive.

Magnificent Mile - End your trip with a shop-till-you-drop paradise here at the 13-block, full mile stretch of city containing some of the absolute best shopping, dining, and hospitality in the Midwest! Explore this ultimate Chicago experience and see why this is considered to be at the center of all that makes Chicago an international destination.

  • Shopping - Shop Coach, Prada, and Burberry before heading over to Macy’s, the Hershey’s Store, and H&M, providing your group with top-notch retail therapy!
  • Dining - There’s something for everybody in your group here on the Magnificent Mile, offering a melting pot of ethnic, gourmet, and fast food proven to please even the pickiest of taste buds.