Weekend Guide: Chicago, Illinois

Ryan & Andrea explore the Windy City – from a comedy club to river tour to deep dish pizza!




Several different people recommended the Architecture Tour to us, and I’m so glad we did it!  It’s really more of a tour of the city, than an architecture specific tour.  It was a 1 ½ hour boat ride through downtown and they told us about the history, notable buildings, and about life in the city.  We got to see everything from a much better vantage point than those crowded city streets. There was a bar on board too – always a fun bonus!

Chicago Architecture Tour | Chicago River | Chicago | Illinois


It’s iconic – you gotta see it!  It’s located in Millennium Park which is a nice area to walk around and people watch.

The Bean | Millenium Park | Chicago | Illinois

 the signature lounge

Located on the 96th Floor of the John Hancock Building, the Signature Lounge is a fun place to see the view and grab a drink.  (Much less crowded than the Sears Tower observation deck!) We got a drink in the lounge, but there is also a (pricy) restaurant where you can have dinner.  There is often a wait to be seated at the lounge, so try to arrive at an off time.

TIP: Girls, you have to check out the womens’ restroom!  You’ll see why when you get there. 🙂

Drinks at The Signature Lounge | John Hancock Building | Chicago | Illinois

the second city comedy club

We saw the comedy show #DateMe at The Second City Comedy Club.  It was was a parody on OKCupid and we loved it!  It’s a nice theater, and they had a lot of fun shows on their lineup.  We wanted to check out a different area of town – north of downtown.  There are several theaters in this area in between Old Town and Lincoln Park.  We ate dinner in Old Town – on Wells Street – before the show and it was a cute area if you’re looking for more of a locals’ hangout.

The Second City Comedy Club | #DateMe show | Lincoln Park | Chicago | Illinois

navy pier

Unfortunately we didn’t have time to make it to the Chicago landmark, Navy Pier, but it sounds like something worth checking out.  There are museums, an IMAX theater, ice skating, a ferris wheel, shopping, live music, and other special events.



When in Chicago, you MUST eat the deep dish pizza!  Pizano’s is located across the street from Millennium Park.  We had a great experience – awesome pizza, awesome waiter, fun/casual atmosphere.

Pizano's deep dish pizza | Millenium Park | Chicago | Illinois

lou malnatis

Lou Malnatis was also highly recommended to us for good deep dish pizza, but unfortunately we didn’t have time to check it out.  Next trip!


swissotel chicago

Swissotel Chicago was in a great location, overlooking the river, north of Millennium park.  The room was great!  No breakfast included though.

Swissotel Chicago | Chicago River | Chicago | Illinois

View of the Chicago River from our room


We took the trains, buses, or walked everywhere and it was very easy!  We also took the train to/from O’Hare airport into downtown, and there is a line to Midway airport as well.  There’s no need to rent a car if you’ll be in the city the entire time.

Other Travel Guides you Might Like:

New York City, New York – Art Lovers’ Tour of New York City

Cape Cod, Massachusetts – Beaches and Lobsters: Cape Cod, Massachusetts

Portland, Oregon – Get Weird & Experience Portland, Oregon

Las Vegas, Nevada – Guide to Gambling and Eating in Las Vegas, Nevada

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Travel guide to visit Chicago, Illinois: Visit iconic Chicago tourist sights & eat deep dish pizza. | wornpassports.com

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