• Saturday, October 24, 2020

what to do in Chicago

Sweet Home Chicago
July 22, 2020
By , Founder

Good For: Couples, families, singles, solo travelers, and groups of friends. Everyone and anyone, unless there is something wrong with you, will have a great time in Chicago.

When to Go:  Chicago shines during the summer months.  In normal times it has the best street festivals in the country, but even in current COVID times they’ve adapted to social distancing and created pedestrian zones during the weekends with outdoor tables on the streets and even these cool greenhouse (more on that later) dining options.  Skip winter which is brutally cold unless you’re in the area for the holidays, in which case Michigan Avenue has one of the prettiest light displays to get you in the festive spirit.  

Suggested Stay: A long weekend of 3-4 nights 

Where to Stay:  Chicago hotels are so good that we’ve dedicated an entire article since we can wax poetic about the excellent hotel options in the city.  Check it out here, where the nutshell is: 

·      The Peninsula.  The most luxurious of the luxurious hotels in the Windy City.

·      The Park Hyatt.  For the modern aesthetic on Michigan Avenue and for those who are into their points accrual.

·      Nobu Chicago.  The hottest hotel in town.  You get most favored nation status for the Nobu Rooftop and eventually Nobu when it opens in a few weeks, which is the most coveted restaurant in town. 

·      The Four Seasons.  Move your family in for a long weekend where kids are treated like VIPs.  

What to Do:  Besides eat, eat and eat – Chicago has some of the best restaurants in the country – this city has an actual beach and stunning waterfront.  Everyone who lives in the US should visit Chicago at least once if not more.  

Architectural Boat Cruise:  In general you couldn’t be paid enough money to get on a boat in this COVID world, except for a cruise on Chicago’s First Lady.  Entirely open air and modified for social distancing to keep everyone safe, this is maybe the most unexpectedly enjoyable experience in the city.  Even as a frequent visitor this is one of the touristy activities we enjoy every time.  

North Avenue Beach.  Yes, there really is a beach in Chicago, and North Avenue is the best of them to take in the Chicago skyline and even take a swim in Lake Michigan.  Catch a game of beach volleyball, or in COVID times bring your own team to soak in the sun for a day.  

Michigan Avenue.  This is the grand dame avenue of Chicago, with the high end shopping.  A walk from the Chicago River up to Oak Street Beach will have the most international traveler wondering how they have not yet been to Chicago.  Make sure to hit up Oak Street which has all the haute couture international brands and go off the path a few streets over to Ikram, which is the fashion forward place to shop in Chicago.  We always pick up some Chanel treasure on visits. To the West of Michigan Avenue is what is known affectionately as the “Viagra Triangle” for the classic restaurant scene of Gibsons.  

Hang Out in Lincoln Park.  This includes the Lincoln Park Zoo, which as an all-outdoor venue open year round, makes for a scenic walk, even if you don’t have kids. Lincoln Park is the classic Chicago neighborhood with townhomes, local bars and tree-lined streets, which can make you just for a moment flirt with the idea of moving to Chicago.  Anchored by Armitage Street with charming shops and cafes, this is where to feel local. 

Millennium Park.  The opposite of Lincoln Park, this is where to feel like you’re visiting Chicago as a tourist.  The famous bean and skyline as well as Grant Park, where in normal times is the center of the major Chicago festivals.  

Check Out Trendy Bucktown.  The original of the trendy neighborhoods that begin to gentrify over 20+ years ago, we like that even with the multi-million dollar homes, they’ve still retained their grit.  

West Loop Meander.  This may just be our favorite neighborhood in Chicago.  The old fish market area that has been gentrified, this channels the vibe of the old Meatpacking district in New York before it became the center of Restoration Hardware and big brands.  It’s a construction zone right now with the luxury condo building to support the Google Chicago HQ that anchors the neighborhood, and has some of the best eats in the city.  

Hotel Hopping. This is one area where Chicago has NYC beat by a mile.  Check out our article on the best hotels in Chicago, which also have some of the best places to have lunch (roof deck at the Park Hyatt), drinks (outdoor bar at The Peninsula) and dinner (rooftop at the new Nobu hotel).  

Culinary Scene.   Chicago, indisputably has some of the best chefs and food in the country.  What we love about this scene is that they know their roots in comfort food and aren’t shy about elevating and adding to the creativity.  From the savory éclair filled with a French onion soup cream at the Loyalist, to Grant Achatz’s Alinea empire taking fried chicken to new heights, or keeping it real with Bandit’s Disco Fries, which are a riff on the iconic Chicago cheese fries (a must when  you are in Chicago) to deep dish pizza, you can eat non-stop all weekend.  We have our list, and we may even have to do a whole feature on Chicago dining.  Make sure to hit up a modern steakhouse like RPM or Mastros to round out your Chicago culinary experience.