“Must See, Must Do” Chicago Sightseeing Recommendations

Still More Info/Pics to Come. Stay Tuned.

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Laid Back Lifestyle

It is fitting that Chicago is located in the Midwest in between two great cities of San Francisco and New York: Chicago is the ideal “mixed breed” between the two.  It is a major cosmopolitan city with a “small town feel”.  Chicago has the “numerous buildings, skyscrapers, diverse influential music and the arts” of NY and the “laid back feel of the different neighborhoods” of San Francisco.

What’s it feel like to walk through Chicago

The center of Chicago has similar hints of the cleanliness feel of Gaslamp District in San Diego as well as a resemblance of Portland modern architecture.  While walking around Millenium and Grant Parks or even the Old Town, Gold Coast, Lincoln Park neighborhoods during the day, you will be surprised to find a quiet peacefulness, as well as the lack of thousands of people, jam packed together, hustling and bustling as compared to New York.  As you walk more into the Downtown area and the Magnificent Mile, you will feel the energy of a spacious vibrant city and, perhaps, flashbacks of a “modern concrete Paris” with the river flowing through the middle of the city, trains/metro subway speeding over bridges, and beautiful skyscrapers everywhere. 

This city has such rich character in its buildings, history, urban planning, unique neighborhoods, the giant lake, and diverse population which includes African American, Caucasian, European (Ukranian, Polish, Swedish, Russian, Italian, and much more), Indian, etc.  In addition, the people of Chicago are very friendly, hospitable, down to earth, and have such a sports city pride.  Yes, the winters and blizzards are probably one of the harshest, but the people of Chicago love their city with a passion.

Post Modern Architecture

Compared to all the cities in the US, Japan, and Europe thus far, Chicago wins the Travel Ganas Award for Post Modernism Architecture!  On the Architectural River Boat Tour, you will notice the various colors, shiny reflective textures, sizes, architectural shapes of buildings mixing in various materials of glass, steel, concrete, brick, etc.  You will also learn on the tour that when a building was built it often “mimicked” a style of a previous building and incorporated a brand new style as if the buildings were “artistically” speaking to each other.




The CTA site is really great to help you find routes and schedules for trains and buses. It makes traveling super easy.


You should download CTA Bus Tracker so you know how long it takes before the bus gets to your location or take the metro/subway.



All of these sights can be done within 3-4 days if you have the “Travel Ganas”

 *** = Absolute Must!





1. *Museum Campus

Photography Museum

Museum of Science and Industry

Field Museum

Soldier Field

Adler Planetarium


2. Shedd Aquarium

  • Tickets are about $26 – one of my favorite spot to visit in the city! Beluga Whales!
  • http://www.sheddaquarium.org/
  • * There’s a hot dog cart right outside the museum that serves really good Chicago hot dogs!

If you want to shop, get on State Street.

Check out the view. The best view of the skyline is here.








3. ***Millenium Park




4. ***“Bean” (Cloud Gate)




5. Prizter Pavilion

other interesting art work/sculptures in the park.



6. **Art Institute Chicago Museum

Wide collection of art from different places and time periods. You can spend a few hours here. Tickets are about $18 for adults.



7. Grant Park




8. Buckingham Fountain

(Fountain from Married with Children)






10. ***Chicago Architectural Tour

  • I’d recommend using Shoreline or Wendella.
  • Shoreline docks at Navy Pier, so it might be farther if you are not already planning on being there.

Wendella docks on Michigan and Lower Wacker. It’s definitely better to make reservations, and cheaper on the week days.

Shoreline – http://www.shorelinesightseeing.com/ (312) 222-9328

Wendella – http://www.wendellaboats.com/  (312) 337-1446

Architectural River Boat Tour



11. *Bike along the lakefront

Chicago’s small enough to see a lot just from biking. You can start around Waveland Ave or Belmont Ave. Bike down to Navy Pier or further. Bikes cost around $10 an hour.

  • Drive outer Lake Shore Drive into the city for a great view
  • Beer Garden
  • Water Taxis






River North/Magnificent Mile



12. **Magnificent Mile (Michigan Ave)

Get off at either Clark / Division or the Chicago stop from the red line and walk south)

It’s the 5th Ave of Chicago! Tons of shopping, tons of people so be careful of pickpockets, but it is generally very safe.



13.  *Willis Tower/Sears Tower Sky Deck 

tallest building in the US, best view of the city all around, they had the new clear class walk out now.

They have the new skydeck..check out the pics…scarrry…and basically the pictures speak for themselves

get tickets for the fast pass for 30 bucks



14. ***Signature Room at the 95th – John Hancock Center

Lunch buffet (Monday-Saturday) for only $20/person. Small selection of good food, and amazing view of the city! You will get a better view of Chicago here, than from the Sears tower. Make reservations in advance. (312) 787-9596


  • Museum of Contemporary Art
  • Gino’s East
  • Pizzeria Uno
  • Purple Pig, Xoco, Hubbard St etc




15. Lincoln Park

Lincoln Park Zoo – It’s free, but far from downtown. There are buses that take you there so it’s not so bad.



Old Town (slight west/north of River North)


16. *** Second City Improv

Slso has cute bars/restaurants in the area

Chicago’s most famous improv troupe, boasting alums like Tina Fey, Mike Myers, Jim Belushi to name a few! Check out their Main Stage show (I think it’s called “Spoiler Alert”) – buy tickets in advance. $27.


Hot Tix



17. Gold Coast

nice neighborhood, homes, interesting architecture



Lakeview (north of the city) 

18. Go to a Cubs Game!


very cute neighborhood, with a lot of young people.


19.  Wrigley Field

If you’re big baseball fans, this is where the Cubs play in



20. Untouchable Bus Tour


tour guide dress up as mobsters and take you around to all the Al Capone sites and tell you about the mob life


19. Street Fairs and festivals

especially in the summer.

Lots of free concerts, festivals, etc.







Useful Chicago Sightseeing Websites








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