a city by the water

They don’t call it the windy city for nothing, so pack your finest coat. Regardless of temperature (it is beautifully warm in the summer, by the way)- Chicago is wonderful. Often referred to as the second city, or New York’s little brother- Chicago offers the very things we collectively look for in a booming metropolis. There’s exciting restaurants, sports teams, parks, culture and of course- great bars.  But it’s the charming and unique neighborhoods, that make Chicago magic. If you’re planning to hit up the city, this guide is your (free) sherpa for 48 hours worth of fun.


If you like a hot chocolate (who doesn’t) then check out Mindy’s Hot Chocolate, they have a earth moving selection of flavored hot chocolates, with a tasty brunch menu too. But be warned-  the drink is so filling you may not need too much. Like- ever again.

If a simple coffee and pastry is more your style then check out one of these: Osmium Coffee Bar, Sawada Coffee, or Ipsento Coffee. Chicago has more than it’s fair share of hipsters– and with hipsters comes great coffee.

a large reflective sculpture with Millennium Park in the backgroundMillennium Park

Chock full of tunning architecture, sculptures and design work, Millennium Park is worth a chunk of your time, without a doubt. And noot just for that classic picture in the famous reflective ‘Bean’ sculpture, though it is very cool too! Millennium Park is a great insight into city planning, cultural gatherings and life near the river. When the weather is nice- there’s  an outdoor music theatre, the Jay Pritzker Pavilion, so be sure to check out if there are any good events on while you’re in town.

Boat Tour/River Cruise

If it’s your first time- sometimes you’ve just gotta join the tourists. One of the best ways to see the second city is by boat- so going back to that “bring a coat” joke- seriously- bring a coat. Cruise along the river to take advantage of below “ground” vantage points of the spectacular skyline and surrounding lake areas.

Plenty of companies offer tours, so do some research to find one that best suits you and your style. On that note- there are dinner cruises, in case a standard day trip isn’t going to cut it.

a city skyline with a body of waterLunch

If you’re a fan of Mexican food, then you’re in luck. Chicago for some odd reason (named Rick Bayless) has some of the very best Mexican restaurants in the world- even including Mexico! Top Chef Masters winner Rick Bayless has the iconic Frontera Grill and Topolobampo, while another Michelin starred master- Carlos Gaytan brings Mexique, which serves delicious French inspired Mexican cuisine. Of course if Chicago is all new to you- you need to give some deep dish pizza a whirl. It’s a staple.

Lincoln Park Zoo

This can be a fun afternoon out, and it’s one of the last free zoos in the country worth going to. With over 200 different species of animals, you’re bound to spot your favorite. The location is ideal for hopping around Chicago’s upscale neighborhoods and well spread out to move at your own pace. Wander around the zoo-see the big cats and then  venture over to the park along the water, which offers up one of the best views of the Chicago skyline.

a close up of foodAlinea

When you happen to be feeling flush, fancy and in need of a second mortgage- you must eat at the 21st best restaurant in the world (2017), and a former top 3- Alinea. You may have seen it on Netflix’ ‘Chef’s Table. If you need a refresher course- it’s the one where the entire table is used to make a modern art painting that resembles dessert. Serving a tasting menu of a modest 18-22 courses, you’re guaranteed to enjoy the most inventive, artistic and creative food you will ever witness. Make sure to plan well ahead for a reservation though- despite the price tag, it’s a tough table to snag.

It’s 5 O’Clock Somewhere- So Here Are Cocktail bars

If you fancy more of a night out and are into good creative cocktails then Chicago has a lot to offer. They also do great beer and other things too, just FYI. We love The Violet Hour, The Aviary, Mezcaleria Las Flores (especially if you’re a fan of Mezcal, we wont tell) and Billy Sunday. For ideal night time fun- plan on positioning yourself  in either the Lakeview, Wicker Park or Logan Square areas. Can’t go wrong, unless you drink too much- then that’s on you.

a city next to a beachBeach? Oh yes! 

Obviously this is for the summer months- but there really are (extremely) hot summer months, with temperatures to rival any tropical paradise. Chicago has a really cool beach scene, and thanks to the lake- water bright enough to make you think you’re somewhere fancy.

For an enjoyable, unexpected Chicago experience, make your way to one of the lakefront areas where sandy beaches, happy people and views of sailboats await. Oh, and if you are easily bored at the beach- there’s great shopping nearby. Aim for North Avenue Beach, Montrose Beach and Oak Street Beach.

City Views

If you’re not too scared of heights and don’t mind tourist fodder- head to the Skydeck on the 103rd floor of the Willis Tower. There are beautiful, panoramic skyline views- but perhaps most importantly, there’s a glass bottom balcony. Look straight down, hundreds of feet below you and don’t forget to breath- or to take the pictures you came to take.  Though the Tower is awesome, if you’re a more unique travel experience person- consider instead capturing the city’s beauty from the ground. Lakeshore drive and all parts west of the city offer excellent skyline views- without all the tourists. Just in case tourists get on your nerves..

a baseball stadium with a crowd of people watchingExtras

Sports fans rejoice. We’ve got the Bears, Cubs, White Sox, Blackhawks and even some curling. Chicago sports fans are manic and attending a game is always a worthy experience. For those more art than ESPN inclined, Chicago will not let you down. There are excellent museums and art galleries well worth a visit: Art Institute of Chicago, Museum of Contemporary Art, and The Field Museum of Natural History. The city happens to have more impressionist paintings than anywhere else on earth, outside of Paris. Not too shabby for New York’s little brother/sister.

Enjoy your trip. Any additions, Chicago experts?

Gilbert Ott

Gilbert Ott is an ever curious traveler and one of the world's leading travel experts. His adventures take him all over the globe, often spanning over 200,000 miles a year and his travel exploits are regularly...

Join the Conversation


  1. 57th Street beach is nice is far less crowded! It’s also right across from the Museum of Science and Industry. The Southside definitely worth a look!

  2. As long as you are at Millennium Park, head across the road to the old Public Library. The whole place is done in wonderful mosaic tiles, and the glass ceiling was made by Tiffany….just like Gallerie Lafayette in Paris. There are some small art exhibits there also. If you like the arts, stay at the Palmer House, next to the “L” line, and the art museum (one of the best in the country) and the symphony center are easily within walking distance. If you have kids the aquarium is excellent.

Leave a comment

Your email address will not be published. Required fields are marked *