Chicago, Illinois-trip planning essentials

Chicago is probably my favorite city in the United States. While I used to adore New York, I’ve long since moved on ever since my first visit to the Windy City in 2008. It has most of what New York has, just without the mobs and packed streets (at least in the touristy areas). Since then I’ve been there two other times and with each visit I can’t wait to return for my next one. This planning essentials post is going to be a combination of all three of my visits to there.

Hard Rock Hotel: We booked this hotel as part of a package and secured a great rate in doing so, but I’m not sure if I’d want to stay there again. It’s located in the Loop area and while situated directly on Michigan Avenue, it’s on the “other” side of the river (the side opposite the Water Tower) and I just have preferred staying on that side. While Hard Rock hotels are supposed to be themed, with each floor at the Chicago location advertising a certain one (i.e. the Rolling Stones floor, the KISS floor), we were on a floor sans theme, so that was somewhat lackluster. While there is an on-site restaurant and bar, we didn’t venture into either, as no doubt both were on the pricier side and we were much too anxious to see the rest of the city. (Our first visit was in July while our other two visits which were in February and considerably colder).
Marriott Residence Inn River North: I just loved this hotel and the neighborhood that it’s in. While there are certainly tourist-geared facilities and venues in River North, it’s more of a residential neighborhood, which allowed me to imagine my dream of actually living there one day. The Residence Inn and Springhill Suites are located in one building, sharing a lobby and other guest amenities, but the rooms are located on opposite ends of the building. They’re pretty generic hotels, but at the same time you always know what to expect which is a good thing.
Sheraton Chicago Hotel and Towers: As was the case with our previous two Chicago visits, we booked our stay at the Sheraton as part of an air/hotel package. The hotel is somewhat out in “left field” and is right on the river, so when traversing to and fro there during a frigid Chicago winter, it’s location isn’t its strongest suit. The rooms definitely needed updating but it suited its purpose as a two night base. More about it can be found here in a review I did some time ago.

Le Colonial: Incredible French-Vietnamese restaurant located in the Gold Coast area. Review can be found here.
Lou Malnati’s Chicago Pizza: You can’t go to Chicago without trying the city’s famous deep dish pizza. While countless options abound, I’d recommend checking out Lou Malnati’s. Just be prepared for a wait time as thin crust it ain’t.
Cafe Iberico: I’m a Spanish girl at heart so when visiting new cities I like to try out Spanish places. Cafe Iberico is located in the city’s River North neighborhood. It offers everything from cold and hot tapas to full entrees.
Pizzeria Due: The offspring of Pizzeria Uno which was a quaint local spot before it became a national chain and populated every suburban strip mall known to man. While I preferred Malnati’s, I can safely say that Pizzeria Due is nothing like the Pizzeria Uno chains-different experiences entirely.
Chango Loco: This is a seasonal restaurant located on the Navy Pier. It’s uninspiring Mexican fare, especially since you’re in a city with an extremely large Mexican population and where significantly better options exist. But sometimes your stomach says convenience and not taste.
John Hancock Signature Lounge at the 96th: The John Hancock Tower is another massive Chicago skyscraper. We went for drinks at its lounge on the 96th floor on our second visit to the Windy City. The drinks were expensive and vying for a table near the windows equated to musical chairs, but it was still a neat experience.
Portillos: Chicago-style hot dogs. Need I say more? They are also famous for their Italian beef sandwiches. The staff was also some of the friendliest I have ever encountered in a major city.

Field Museum: Terrific natural history museum. Although somewhat removed from the city’s main attractions, bus lines that originate in the Magnificent Mile section drop you off directly in front. Worthy for both young and old.
Wendella Boat Chicago River Architecture tour: Wendella Boat tours are one of Chicago’s longest running tour outfitters (dating back to the 1930s), so not only do they know their stuff but clearly they’re doing something right. The boat tour was highly interesting and the guide extremely informative. In addition to the architecture themed tour, they also offer a combined lake and river tour as well as a sunset tour.
Navy Pier: At least in warmer weather you have a Ferris wheel, swings, and other carnival style attractions along with other entertainment options thrown in. Pretty good deal, especially if you have young ones. While the rides are dormant in the winter, I’ve read that Navy Pier is a pretty fun place to go to for the Christmas season.
Art Institute of Chicago: Even though the bulk of the paintings I wanted to see were on loan when I visited due to the construction taking place in the wing where they were normally located, it’s still a world renowned art museum.
Sears (Willis) Tower: It’s a legendary icon offering superb views. If you need more incentive to visit check out my review here.
Frank Lloyd Wright House and Studio: Located in nearby Oak Park, this is a must for anyone interested in architecture in a city that has churned out some pretty spectacular buildings and is the birthplace of native son Wright.

There’s plenty more I would like to see and numerous more restaurants I would like to try, but for a first time visitor to the Windy City, you’re off to a pretty good start with these essentials.

The Wrigley Building-a personal favorite

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  • Reply
    Wanderlust Traveler
    April 30, 2013 at 3:33 pm

    Great post! I am so excited to visits many of these places on our trip including the boat tour, Frank Lloyd Wright home, Sears Tower, and of course eating at Lou Malnati’s and having a drink up on the 96th floor of the John Hancock Tower!

  • Reply
    the red headed traveler
    April 30, 2013 at 9:18 pm

    I actually wrote this post a couple of weeks ago but never got around to publishing it. It reminded me when I saw that you were going! I know that you’re going to love it there-so much just awesome uniqueness for lack of a better description!

    Some people say Geno’s is better for pizza but we’ve been “pleased as punch” the two times we went to Malnati’s. My h is clamoring to order the pizzas online, at an expensive rate I might add ๐Ÿ™‚

    Yes, the boat tour was definitely one of the favorite things we did. The architecture in the city is just astounding!

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