3 Days in Chicago

Tate has a very special relationship with Chicago as it is where he was born and raised. Spending his first few formative years in the Windy City allowed him the opportunity to explore the best of Chicago. Chicago is a huge city with many historic sites, amazing museums and of course, delicious food.

Most of the foods that Chicago is known for (deep dish pizza, hotdogs) are not the foods that we would typically seek out during our travels. We have included a few recommendations for where to go if you are dying to try some of these local specialties. Don’t get us wrong, none of this is BAD food, it is just that Chicago’s food scene has become much more sophisticated and we think there are foods a bit more worthy of your time. To be honest, our B list for food could easily be an A list. Check out our recommendations but also do your research to make sure you are dining at the places that suite your appetite and budget! 

 A List-

Restaurants

  • Alinea, Girl and the Goat, Portillos, Schwa, Fat Rice, Ema, Lula Cafe, Mindy’s Hot Chocolate, Sushi-San, Monteverde , Peaquods, Cindy’s Rooftop Bar, Eataly

Local Foods to Try

  • giardiniera, deep dish pizza, italian beef sandwiches, chicago hot dog, gastronomy, malort (only if you’re brave and have a strong stomach), garrets popcorn

Things to See

  • Millennium Park & The Bean, The Art Institute of Chicago, The Magnificent Mile 

Neighborhoods to Visit

  • River North, Wrigley, West Loop, Lincoln Park 

Tours 

  • Architecture Boat Tour

B List

Restaurants

  • Duck Duck Goat, The Publican, Smythe + The Loyalist, Gibsons, The Aviary, Roister 

Things to See/Places to Visit

  • Willis Tower, Logan Square, Navy Pier

Neighborhoods to Visit

  • Logan Square, Wicker Park, Chinatown 

Day 1

Welcome to the Windy City! Get your walking shoes on because today you will be exploring the city by foot. Head out of your hotel and make your way to Eataly in River North to grab an espresso and a breakfast pastry. Spend your time walking around the store to explore the beautiful displays of fresh pasta, seafood, meats and cheeses.  Exit Eataly and head a block east to Michigan Avenue, also know as the Magnificent Mile. Enjoy shopping or window shopping and if it is the winter, looking at the holiday displays. 

Off of Michigan Avenue you can venture to the John Hancock building to get amazing views of the city at the 360 Chicago Observation Deck. There are also activities for those not afraid of heights such as the Tilt. When hunger strikes, head to Ramen San or Sushi San – both off of Michigan Avenue for lunch. Depending on if you want ramen or sushi, both of these spots by the Lettuce Entertain You Restaurant Group will bring you an ambiance of 90s hip hop and most importantly, amazing food.

Once you are filled up, head back to Michigan Avenue and walk south until you get to Millennium Park. Spend an hour or two exploring the park and be sure to visit the famous Chicago Bean. If you are an art fan, don’t miss the Art Institute of Chicago. However you spend your afternoon, don’t miss stopping by Cindy’s at the Chicago Athletic Association for a cocktail, snack and amazing park and lake views. 

If you are like us, you will be ready for a nap at this point. Relax for the rest of the evening because for dinner, you will be going to the coveted Fat Rice in Logan Square. It is hard to describe Macanese cuisine at Fat Rice as it is a blend of Chinese, Thai and Indian cuisines. The flavors are incredible, unique and will fill you up after a long day of walking through the city. Make sure to make a reservation in advance. The food is amazing. Just go. Trust us on this one. 

Day 2

Day 2 is going to take you through a few of Chicago’s neighborhoods that are outside of the main downtown area. Start you day with breakfast at Lula Cafe in Logan Square. Lula does take reservations which are highly recommended on the weekend. If you have to wait for your table, no problem! Walk around the Farmers Market if you are there on a Saturday or explore the many unique shops near the restaurant.  When you are done with breakfast, take a long walk, south, down Milwaukee Avenue and you will soon be in the neighborhood of Wicker Park. On this walk, you will pass many coffee shops, breweries, and stores. Take your time and enjoy these two unique neighborhoods. Hungry for more? Try the famous burger from Small Cheval or a piece of pie from Bang Bang Pie Shop.

When you are through walking and exploring, hop on the Blue Line to the Monroe Station. Get above ground and you will be just blocks from the Willis Tower. Head on up for views of the city and the Skydeck where you can walk on top of a see-through glass floor. Don’t forget to look down! Head back to your hotel and get some rest before your big night out at Alinea. We wrote a whole post about this very special dining experience that you can read through here.

Day 3

We know you are probably very full of food by this point in the trip. No plans for you this morning! Sleep in. When you are ready make your way towards the lake and walk up and down the lake shore path. Venture north and you will make it to Lincoln Park where you can go to the zoo (for free) or head south to Navy Pier. If you head north, we recommend venturing to Old Town for lunch. On Wells, you will find many, many restaurants and bars to enjoy. 

The last stop for your day will be back to Michigan Avenue where it crosses with the river to board the Architecture Tour . This is a very unique tour, done by boat, and will teach you about the history and architecture of the city and is a great way to see the skyline from the water! 

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