Two Days in Chicago – Older Woman Solo

Two Days in Chicago – Older Woman Solo

Chicago’s nickname is the Windy City.  The nickname dates back to the late 1870s.  Then editor Charles A. Dan of the newspaper the “New York Sun”,  wrote that “Chicago was windy because of its politicians being full of hot air.”   If you were to ask someone from Chicago, if that reputation has changed, the answer would be no. Although known for it strong political ideology, Chicago is also known for its beautiful skyline, its diverse neighborhoods, amazing food scene and its architecture.  If you really want to get to know this fine city, up-close and personal, I recommend renting an Airbnb (check out my stay at one in DC) in one of the 77 communities that make up the city of Chicago. If renting a space in someone’s home is not your thing, check out last minute hotel deals from TripAdvisor.

Two days Chicago


How to Spend Two Days in Chicago

Read San Francisco in 3 Days

Day 1

Purchase a Go Chicago Card.  I recommend the all-inclusive Go Chicago Card pass for $135.  The all-inclusive pass allows admission to 26 tours and attractions without having to stand in long ticket lines at each attraction/tour. Download the Go Card App for easy access to your Go Chicago Pass.

Let’s go!

  • Chicago Architecture River Tour – This is an awesome way to view the city.  Use your Go Chicago Pass for admission to Shoreline Sightseeing “Chicago Architecture River Tour”.  It is a 1-hour tour of the Chicago River and the architectural landmarks that are along the river.  There are 2 departure points – Navy Pier or Michigan Avenue Riverwalk (401 N Michigan Ave Plaza – look for the signs).  Recommendation:  board at the Michigan Avenue location.  There’s usually a long wait at the Navy Pier location.
Chicago Architectural Boat Tour 2 days chicago
Going under the Adams St Bridge

Chicago Architectural Boat Tour 2 days chicago
Chicago Architectural Boat Tour

De-board the boat tour at the Michigan Riverwalk (401 N Michigan Ave Plaza) and make your way to the Sheraton Chicago on 301 E North Water for your next tour.

  • BigBus Tour (Double Decker) – Catch the BigBus Tour on Columbus Drive, right in front of the Sheraton Chicago.  Flash you Go Chicago Card and upgrade to a second day for $15.  Big Bus Chicago is a great way to get a feel for the city and provides transportation to most of tours and attraction on your two-day quest.   You can hop on and hop off to explore the city’s attractions such as the Field Museum, Millennium Park, Navy Pier and much more. The panoramic top-deck view is perfect for taking amazing photos of the city.  Recommendation: Can get quite windy top-deck.  Bring a jacket, hat, and shades.
Two days Chicago - the social tourist
Big Bous Tour riding along State Street



Hop off at stop number 11, Navy Pier
  • Navy Pier completed in 1916, Navy Pier has been repurposed several times as a jail for draft dodgers, a training center for the U.S.Navy, and facilities for the University of Illinois at Chicago. Navy Pier has now evolved into a major tourist attraction that includes a children’s museum, a Ferris wheel, a concert venue and tons of places to eat. Recommendation: catch a movie at the IMAX theater or a free performance at Polk Brothers Park. Check out Navy Pier’s Calendar of Events.  
Big Bus Tour two days chicago
Big Bus Tour leaving Navy Pier
Hop off at the next stop (#12 – 835 N Michigan Avenue)


  • Make your way to the Museum of Contemporary Arts (MCA).  Use your Go Chicago Card (membership has its benefits) for admission into the MCA. Founded in 1957, this museum features provocative art and exhibitions meant to inspire the artist in all of us.  Recommendation: Check out the exhibit Takashi Murakami: The Octopus Eats Its Own Leg (until September 24, 2017)
MCA two days chicago
Poster Outside of MCA
MCA two day chicago
Murakami exhibition
mca - two days chicago
MCA Exhibition
Next, you want to open your Uber app, order a ride to the next stop, which will be Frank Lloyd Wright’s Robie House. You can also use public transportation.
  • The Robie House is located 5757 S. Woodlawn in the neighborhood of Hyde Park.  The architect Frank Lloyd Wright designed this prairie-style home that has become an icon in the architecture world for a businessman by the name of Frederick C. Robie.  It was completed in 1910.  Use your Go Chicago Card to gain admission to the tour (tour times).
tour guide robie house two days chicago
Tour Guide in Front of Robie House
robie house - two days chicago
Inside Robie House

Recommendation:  After the tour, stop at Plein Air Cafe (right next door to Robie House) for a refreshing cup of tea.

If you have any energy left after re-charging at Plein Air Cafe, take a 15-minute walk to Museum of Science and Industry
  • Museum of Science and Industry, located at 5700 S Lake Shore Drive, is the last remaining building of the 1893 World Columbian Exposition.  It is now home to the largest science museum in the western hemisphere. What’s great about this museum is there’s something of interest for people of all ages. Recommendation: Check out the Coal Mine and U-505 submarine exhibit. After you finish up at the Museum of Science and Industry, Uber it to Medici on 57th for pizza – 327 E. 57th St.


Day 2

If you upgraded to a second day on Big Bus Chicago, hop on at the Chicago Theater (175 N. State St.), get off at the Willis Tower, stop #3.   Use your Go Chicago Card to bypass the long line for tickets to the Willis Tower’s Skydeck.

  • Willis Tower (233 S Wacker)- The former Sears Tower is now the Willis Tower; so named since 2009, for a global insurance brokerage company.  Chicagoans still call it Sears Tower. It is the 12th tallest building in the world and is home to the highest public viewing area in the United States.  On a clear day in, you can see 4 states – Illinois, Michigan, Wisconsin, and Indiana.  The Skydeck located on the 103rd floor of the Willis Tower features the LEDGE.  It is four glass boxes on the western side of the Skydeck for observing the street underfoot. Recommendation:  Although your Go Chicago Card will bypass the long line for admission to the Skydeck, you will still have a long wait for the elevator ride to up to the Skydeck.  Get your belly full of breakfast at the Original Pancake House (22 E Bellevue Pl) before tackling this attraction.  There’s no vending machine or snack area once you get to the Skydeck. You will be on your feet the whole time so wear comfortable shoes.  The only seating is a metal bench near the bathroom.
Willis Tower - Go Chicago Card
Willis Tower (Sears Tower)


Skyline of Chicago - Two Days Chicago
Skyline for the Willis Tower
Skydeck Willis Tower 2 day Chicago
Skydeck at the Willis Tower
Hop back on the Big Bus, across the street from the Willis Tower


  • Hop off at stop #4 Use your Go Chicago Card to gain fast-pass entry to The Art Institute of Chicago (111 S Michigan Ave) – was founded as both a museum and a school of fine arts in 1871.  However, the Art Institute didn’t find it’s present home until 1893 when the building, flanked by 2 lions,  was built for the World’s Columbian Exposition.  The Art Institute of Chicago houses a permanent collection of more than 300,000 paintings, exhibits, and artifacts.  There is something for the art lover in all of us at this museum.  Expect to spend at least a couple hours in this large museum.  Recommendation: if you get hungry stop by the Terzo Piano for a light lunch and glass of wine.
Terzo Piano Art Institute of Chicago
Terzo Piano at the Art Institute of Chicago
Hop on the Big Bus in front of the Art Institute of Chicago


Art Institute of Chicago - Go Chicago Card
The Art Institute of Chicago
  • Hop off at stop #9 and use your Go Chicago Card to check out the Field Museum (1400 S. Lake Shore Drive) – Founded in 1893 as part of the World’s Columbian Exposition, the Field Museum is home to world-class scientific researchers, extraordinary exhibits and Sue, the T-Rex.  Recommendation: If you’re not all museum-ed out by now, use your Go Chicago Card to check out Shedd Aquarium and the Adler Planetarium.  All three museums (and Soldier’s Field – Home of the Chicago Bears) are part of the Museum Campus (1400-1562 S. Lake Shore Drive).

Hop Back on the Big Bus at either the Field Museum or Adler Planetarium


  • Hop off at stop #13 – The Hancock Building and use your Go Chicago Card to Fast-track to the 360 Chicago Observation Deck of the Hancock Building.  This 100 story skyscraper is the 4th largest building in Chicago. The 360 Observation Deck at the Hancock building has the TILT attraction which is a series of floor to ceiling windows that slowly tilt outside the building to 30 degrees.  The Go Chicago Card doesn’t include the chance to experience the TILT; the charge for that is $7.00.  If you pre-purchase your tickets online (which I recommend) the cost is $6.30.  Recommendation:  If you are looking for more of a chilled-out experience the observation deck has wide-wooden bleacher-like seating. Perfect for taking in the breathtaking views of Chicago.
The Social Tourist - Two Days Chicago
Me, chillin’ on the bleacher seating at 360 Observation Deck


the social tourist - Two Days Chicago
skyline view from Hancock Building


Social Tourist - Two Days Chicago
View from the Hancock Building


And there’s a bar/cafe to grab a snack and something to sip on.
the social tourist - 2 days Chicago
Snacks and Libations at 360 Observation Deck Hancock Building

the social tourist - two days Chicago

Looking South along Lake Michigan from the Hancock Building

You did it – Two Days in The Windy City

Whew! It’s a lot to process in two days but well worth it. This was only the tip of the iceberg.  There’s more to come as I continue to show you the best of my city.
Goodbye for now, until next time!

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