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:  

Yes, you can come to Chicago to eat, eat and eat.  Chicago has some of the best restaurants in the country. Besides that though, 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 that is, for a cruise on Chicago’s First Lady.  The cruise is entirely open air sans pandemic, and today, 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. From this vantage point you get to take in the Chicago skyline and even swim in Lake Michigan.  Make sure to also catch a pickup 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. However, also 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”.  It’s where you go in Chicago for the classic restaurant scene of Gibsons and Tavern on Rush.

Hang Out in Lincoln Park

This includes the Lincoln Park Zoo, which as an all-outdoor venue open year round.  The zoo 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.  It’s charming enough that it can make you just for a moment flirt with the idea of moving to Chicago.  Anchored by Armitage Street with quaint 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.  This is home of the famous bean sculpture and has the iconic skyline view of the Loop.  It is also the location of Grant Park, where in normal times is the center of the major Chicago festivals.

Check Out Trendy Bucktown

Bucktown is 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 over the past 25+ years. This area channels the vibe of the old Meatpacking district in New York. That is of course, before the Meatpacking 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.  However, it 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 keep it real with Bandit’s Disco Fries, which are a riff on the iconic Chicago cheese fries. Yes, cheese fries are a must when  you are in Chicago.  Speaking of musts, deep dish pizza is on that list too. 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.