Chicago Recommendations

Recently some friends asked for some recommendations on what to see, do, and eat while in Chicago. Since I’ve created this list before a few times now, I figured I’d finally create a blog post on it so that I could easily point to it and also update it if I think of other things to add to it. It is geared more toward visitors downtown with limited time who can only get around by taxi or public transportation. If you will be there for a week or more it would be good to get a guide book. I haven’t linked everything or added exact locations to everything, but today with the internet you can likely find it easy with a search. BTW, I’ve generally listed they by my preferred or most recommended.


One of the best ways to get a good overview of the rich architecture history of Chicago is to take the river boat tour by the Chicago Architecture Foundation (CAF). It is the best opportunity to get a crash course on the history of Chicago architecture and you also get a pleasant ride through the urban canyon surrounding the river. The CAF also has numerous walking tours that they run out of their store at Jackson & Michigan. Just to the west of the CAF, there is a place that offers Segway tours.

Millennium Park and the Bean – It has now become one the must-see in Chicago. Cloud Gate ‘the Bean’ is a large mirrored sculpture in Millennium Park. On a sunny day or at night, the reflections on it are amazing. Millennium Park also includes the Crown Fountain which features towers and each end which display faces of selected strangers. The Lurie Garden is a large sculptured garden displaying many native species. The Pritzker Pavilion by Frank Gehry with the tubular canopy over the audience area is an interesting sight. To the east of the band shell is the BP pedestrian Bridge also by Gehry.

The lake is one of the greatest assets of Chicago. It is greatly utilized (maybe overly) in the warmer months and has a 20 mile long park stretching most of the city’s lakefront. The park includes museums, band shells, marinas, playing fields, and beaches. Oak Street beach and Ohio Street beach are the closest to downtown with Oak Street at the north end of Michigan Avenue and Ohio Street just north of Navy Pier. Lincoln Park Zoo to the north of downtown is free and has an extensive collection of animals including a farm.

If you have a chance, it is interesting to take a ride on the El (elevated train) around the Loop. A recommended short route would be to catch the train at the Randolph stop going south on the Pink line over to the Quincy stop. The Quincy stop is the oldest station in the system and has been restored to its original look. At Quincy reboard on an Orange Line train which will bring you full circle around the Loop back to Randolph.

In my opinion, the best view of the city is from the John Hancock. You could pay to go up to the observatory or my preference is to take the elevator (enter off of Chestnut) to the Signature Lounge (not the Signature Room) on the 96th floor. For the same price as the admission to the observatory, you also get a high-priced drink and a seat to watch the city bustle below you. If you go an hour before sunset, you can sit and watch as the city changes from day to night. My preference for the Hancock is also due to the view to the north over Oak Street Beach along the lakefront. If you do go to the Hancock Observatory, they have a skating rink. The Sears (Willis) Tower Observatory has an interesting all glass space with a glass floor that projects from the side of the top. Both observatories offer explanations of what sights and buildings you are actually looking at.

Since I practically grew up at Wrigley Field, I must recommend you go there to see a game if they are playing. A day game if possible. And before or after you go in, stop by Bar Louie a couple doors south on Clark. I usually grab a sandwich and bring it in with me to the game.

The major shopping area is north Michigan Avenue from the river north to the John Hancock Building. Stores include an Apple Store, Nordstroms, Neiman Marcus, Tiffany’s, the Nike Store, Sony, Disney, Banana Republic, FAO Shwartz, etc. For more high-end shopping, check out Oak Street west of Michigan Avenue.

Some notable places include the Chicago Cultural Center, the Macy’s Store, and Daley Plaza. For the Cultural Center, enter at the south entrance and climb the stairs to the top floor. The stairwell and the atrium at the top of the stairs were done by Tiffany. Another work of Tiffany can be seen by entering the Macy’s store at the southwest corner and looking up at the ceiling. Daley Plaza contains a Picasso sculpture that has come to represent Chicago. Across from the plaza is an equally large sculpture by Miro.

As for Navy Pier, I can’t say I really recommend it. There is the Ferris Wheel which gives a good view of the lakefront and the city. And you can walk the length of the pier in order to get far out into the lake. But much of it is touristy and some of it is just plain a rip-off.


There are a ton of world-class museums in the city and you really can’t go wrong with any of the following. My favorite is the Museum of Science and Industry (MSI). So much to do and explore including a huge model train set, a German submarine, an Omnimax theater, and a ton of hands-on science exhibits. The only downside to the MSI for visitors from out of town is that it is not within walking distance from downtown. Next is the Art Institute with a large selection of all types of art including numerous paintings of my favorite style ‘Impressionism’. The Aquarium has numerous exhibits including a dolphin show overlooking the lake. The Field Museum is one of the best natural history museums including real mummies and dinosaur skeletons. The Adler Planetarium has recently been expanded and includes multiple theatres and hands-on exhibits. The Museum of Contemporary Art near north Michigan Avenue also has an excellent collection.


There are tons of good places to eat. I would say that the signature dishes are Chicago style pizza, the Chicago style hotdog, and Italian beef.

For Chicago style pizza, I overwhelmingly recommend Lou Malnati’s Pizza on Wells just north of Hubbard. Be sure to get the deep dish with butter crust. The traditional type is sausage with or without mushrooms. Don’t bother ordering appetizers since the pizza will be more than enough. Gino’s East (also on Wells) used to be quite good, but when we were there last summer, I didn’t like it. I’ve heard that Giordano’s and Pizzeria Uno are also good, but I actually haven’t tried their deep dish since I always go to Lou’s. That said, I remember that the thin crust pizza at Giordano’s is quite good.

For Chicago Style Hot Dogs, the Weiner’s Circle up on Clark is my favorite, but it’s not that close to downtown. They have cheddar fries that are horrible for you, but I love them. Downtown there is a Gold Coast Dogs on Wabash between Lake and Randolph and they also have a location at O’Hare on the L concourse. There is also Max’s takeout on Adams between Wabash and State.
For lunch, there is the ubiquitous Corner Bakery (which I call Corner Robbery due to the prices). They are all over the place and they have good sandwiches, salads, and baked goods. My favorites are the pesto chicken sandwich, the DC chicken salad, and a brownie.

My favorite place for breakfast or brunch is Wishbone in the West Loop (a bit of a hike from downtown). Great southern cooking and my favorite is the shrimp & cheese grits.

A very good Cajun place is Heaven on Seven located at Rush (one street west of Michigan) and Ohio.

The Cheesecake Factory isn’t exactly unique to Chicago, but it is in the basement of the Hancock building and they have both good food and good cheesecake.

If you like Greek food, you need to go to Halsted between Van Buren and Lake. Athena and Santorini are recommended by friends. We’ve been to Costa’s and I remember that it was good.

La Scarola is an Italian restaurant that has been recommended by friends. It is on Grand, past the river, but before Halsted.

Just southwest of downtown is Manny’s at Jefferson and Roosevelt. Classic deli that is cafeteria style.

Farther away from downtown is El Barco recommended by a friend. It is on Ashland between Division and Augusta. Even farther is Smoque on Pulaski just south of Irving Park Road. I’ve heard that place has a line out the door. Same for the sausage specialty restaurant Hot Doug’s on California between Addison and Belmont. A friend also recommends Kuma’s Corner on Belmont west of Elston for burgers and heavy metal.


Blue Man Group is a great show if you have a chance to get tickets. The Chicago Theatre always has some interesting acts or shows coming through town. There is also the House of Blues which has good music acts. Buddy Guy’s Legends down on Wabash at Balbo also had shows every night.

For Chicago Blues music, there is Kingston Mines up on Halsted north of Fullerton. Not far from there is B.L.U.E.S which also has live bands every night. For jazz, my uncle recommends The Back Room on Rush Street north of Oak. Farther away, there is The Green Mill up on Broadway, north of Lawrence.

If you think of anything else to recommend, leave a comment and I’ll add it to the list.


~ by Frank on March 26, 2012.

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