I flew to Chicago to reunite with my traveling sisters Janie, Wendy and Celle for the Columbus holiday weekend which also happened to be Janie's celebratory birthday. We all decided to meet somewhere in the middle since Janie is flying out of Los Angeles, Wendy from Houston, Celle from La Guardia and I drove to Baltimore Washington International (BWI) to catch my flight to Chicago Midway (MDW). 

The Traveling Sisters

We rented a car so we could drive around and also since we were staying closer to the airport (MDW). It wasn't too bad driving around Chicago. The traffic was manageable and we seem to get to places in a decent length of time. We had lunch at The Capital Grille coz we were craving for succulent seafood and prime steaks. It was the perfect restaurant for upscale dining/birthday lunch. 

When in Chicago, you should definitely check out Michael Jordan's statue at the United Center. Then go to the tallest building in the city at the Willis Tower (formerly Sears Tower) and step onto the Skydeck Ledge while looking down on the smaller buildings below you. The basic admission ticket is $19 for adults (ages 12 and up). For lunch, go to Shaw's Crab House for quality seafood. 

Chicago Segway Twilight Tour

When in Chicago, you must ride the segway tour at night. 

There is something magical about the twilight tour with the city lights. To book your segway tour, visit Abolutely Chicago Segway Tours. The Grant Park Twilight Segway Adventure is available daily starting at 6:00 PM for approximately 2 hours. The price per person is $60 but if you book ahead on their website, the online special pricing is $49.95 per person. For dinner, go visit Giordano's for the famous deep dish pizza. Make sure you come hungry coz it takes about 45 minutes to cook the deep dish pizza.

When in Chicago, make sure you book the Lake and River and Architectural Tours. Seadog Chicago offers a 75-minute tour for $31.95 per person. They are located at the Navy Pier a short walking distance from the Ferris wheel. The tour includes amazing views of famous buildings and unique architecture along the Chicago River and an exciting speedboat ride along the lakefront. For lunch, visit the Riva Crabhouse in the Navy Pier if you have a reservation. Otherwise, if you're lucky you might just get a table without a reservation like we did. The second floor of the restaurant offers unparalleled views of the Chicago Lakefront. 

Tip: parking at the Navy Pier is a flat rate of $25 per day unlike in the parking garages downtown where the rate goes up every additional hour.

Also when in Chicago, do not forget to visit Cloud Gate or The Bean in Millenium Park. I would strongly advise you to go there early in the morning around sunrise to avoid the crowd.

Cloud Gate


  1. This is so informative and it's very helpful! Thanks a lot!! :)

  2. You're welcome! And thank you for your love and support!

  3. Awesome, thank you!

  4. I'm from Brazil. We are going to Chicago (my wife and I) for a 9-day vacation trip next week. Thanks a lot for your suggestions!!

    1. 9 days?! Wow! You're definitely going to see a lot and more. Keep in mind, Chicago is very windy around this time of the year which was also the same time my friends and i were there and at night it could reach freezing. So definitely bring gloves and scarves. Bring a light jacket as well and October 12 is Columbus holiday and the marathon is also happening around this time of the year so some of the attractions may be unavailable that day due to road closures. Have fun and enjoy your trip! ;)

  5. Yeah, so very informe really, really. Tea cake and kahlua is good 4RRRREAL. TH