Deep Dish Pizza! No Chicago trip is complete without it!

Lou Malnati’s is my favorite of the Chicago “Big 3” of deep dish pizza (the other two are Giordano’s and Gino’s East – Giordano’s is a legitimate second). Definitely get the Malnati Chicago Classic, it might be the best pizza I’ve ever had. This location is my favorite too, it’s in the Gold Coast which is the nicer more ritzy downtown area with a ton of good shopping and restaurants.


Also, Chicago Pizza and Oven Grinder makes pizza-pot-pies that are out of this world! No reservations and walk in and cash only, but this is a truly revolutionary pizza experience. This place is seriously one-of-a-kind, and amazing! (Lincoln Park)


EATALY Chicago

A Mario Batali owned Italian dining experience with 20+ “mini restaruants” (i.e. cheese, wine, pasta, meat, nutella, gelato, etc.) and high-end Italian market with absolutely incredible food that is really fun too! This place is unbelievable, locations in NY, Chicago, and LA coming soon!


Al’s Beef – Super dank and greasy italian beef sandwiches (the “Philly cheese” of Chicago – downtown and Wrigley):


For an authentic “Old Town” Chicago experience, check out Twin Anchors for some ribs and a beer. An old Sinatra hangout, and the location of the famous Two Face coin flip scene in The Dark Knight


Cafe Ba-Ba-Reeba

If you like Spanish food and tapas, nothing compares. Awesome place with authentic and AMAZING tapas (and a full sangria selection) in the nice and mellow Armitage district. This is absolutely the best Spanish restaurant I’ve been to since I lived in Spain. BUENO!


Garretts Popcorn

Super delicious popcorn! Definitely get the cheddar/caramel mixed, sounds ridiculous but it’s amazing. Definitely a must-have downtown! Bunch of locations all over downtown, go at an off time or the line will literally be around the block.


Chicago Dogs!

You can get them pretty much anywhere, but you have to get one somewhere before you leave!

Portillos (downtown):

Wiener Circle (Lincoln Park/Lakeview – Famous for reality TV show):

Clark St. Dog (across the street from my old house!):

Wrigleyville Dogs:

For more check out:

Red Eye Suggestions,0,435836.story



  1. Kuma’s Too – awesome, intense, goodness. Heavy metal themed bar with wicked awesome burgers, this is a must, and right by my old place.
  2. Butcher and the Burger – awesome, Counter-style, customizable burgers. Real good stuff.
  3. Au Cheval – never made it here but hear fantastic things!


Activities (for the most part in order of importance)


Tier 1:

THE BEAN! (the millenium cloud) a must-visit photo op downtown, adjacent to Chicago’s famous and very picturesque Millenium Park (often with free concerts and activities):


Hancock Signature Lounge

Instead of paying and waiting in line to head up Sears (now Willis) tower, go to the Hancock building and head to the 96th floor where you can get drinks and enjoy spectacular views from the Hancock Signature Lounge for FREE!


Chicago Architecture Tour

Amazing views and informative history on this 90 minute boat tour that leaves right from downtown! It’s about $25 but well worth it! Wendella is the best company, and leaves right from the bottom of the Wrigley building.


You can walk from the BEAN to Hancock (Wendella boats is halfway in between) and check out Chicago’s MAGNIFICENT MILE which is the most famous downtown street and includes more shopping and sightseeing than you could even imagine.


Tier 2:

Shedd Aquarium!

This is an incredible aquarium with awesome exhibits (i.e. caribbean reef, an ANACONDA, penguins, otters, and dolphins, sea lions, and belugas that do tricks!) that also offers one of the best views of the city as well (looking back from the south side). Aquariums are the best, and this one is definitely worth checking out!



Art Institute of Chicago – name explains it all, priceless art in Chicago’s most famous museum

Next,  Field Museumand Science and Industry are the big ones. Only problem is that they all cost a little cash!


Navy Pier – pretty touristy, but worth a stroll to see the views of the city. Definitely check out the ferris wheel and Jimmy Buffets Margaritaville!


Christkindlmarket – A traditional German Christmas market, supposed to be pretty awesome for drinking, food, and shopping


Ice Skating! Downtown next to the famous “Bean” (the famous Millenium Cloud statue that looks like a giant bean)



Home of the Chicago Cubs’ iconic stadium, Wrigley Field, this is the “frat row” of Chicago filled with countless bars, restaurants, and other fun things to do! Catch a game or go on a tour of possibly the most famous baseball field in baseball or just hit the bars for a good time.


Sports: If you have a chance (and the cash), the Cubs, White Sox, Bears, Bulls, and Blackhawks are worth the price of admission!