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What to do in Chicago - a 3 day hybrid itinerary for active travelers

Updated: Nov 9, 2020

Chicago - view from Penthouses at Grand Plaza

We love short, spontaneous, hybrid travel getaways. Many people may think it’s not possible to mix Active travel with Leisure travel on a short weekend, especially in a major city like Chicago. But that's not true. This waterfront metropolitan gem offers several options for getting outside and staying physically active during the day, so you can guiltlessly enjoy those fantastic restaurants and delicious cocktails at night. So whether a trip through Chicago is for business or for pleasure, here are Paradox Travel’s suggestion on how to keep moving while spending three food and fun-filled days in Chicago.

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Where to stay

Upscale and unique hotels abound in Chicago. If you are a foodie or plan to do some shopping on Magnificent Mile, then River North is an excellent area to make your base. Hotels such a The Thompson, The Westin and The Langham will satisfy the luxury traveler, while Dana Hotel, Ivy and the Gwen offer more boutique alternatives. One of our favorite accommodations, if you are traveling with another couple, is renting one of the incredible 2 or 3 bedroom Penthouses at Grand Plaza. With spacious views and fully equipped kitchens, you can enjoy wine on your own deck with a million dollar view (photo above) after a full day of shopping. Theatre lovers have several moderate choices south of the River or near Millennium Park. If you are Kimpton members, check out The Gray or The Monaco. Hotel Alise offers a more boutique experience and a stay at theWit will not only reward you with great service and beautiful rooms but their rooftop bar has one of the best views in the city.

Millenium Park - "The Bean"

Getting around

Regardless of where you stay, public transport and use of ride services such as Uber or Lyft make it easy to get across town. But I highly recommend giving yourself time and walking most anywhere you go. Not only will you get a chance to burn off some of that last terrific meal, you will also have a chance to view the fabulous architecture that defines Chicago. Down by Millennium Park, you can also rent bikes by the hour or the day. There is a fabulous bike path that stretches 18 miles, passing Soldier Field, the Museum of Science and Navy Pier. Cycling is a fun way to see the waterfront. And you will also cover more territory than you would be able to on foot.

Apogee Lounge - PC the Dana Hotel

Day 1 - A night on the town

Activity suggestion - After you arrive and get settled into your hotel or rented condo, you may as well start thinking about where you are going to start your evening. Any Chicago night-on-the-town will be highlighted with sipping cocktails in one of the several open-air, uber-cool rooftop lounges that this city has to offer. Try either Apogee at the Dana or Noyane at the Conrad.

Dinner suggestions - Are you a foodie looking for creative dining and fantastic flavor combinations? Start out with appetizers and drinks at the Purple Pig Wine Bar, then check out Frontera Grill in the River North area. Are you in the mood for sushi? Niu Sushi or Oysy, near North Side, provide modern and vibrant dining atmospheres and fresh, creative combinations.

Buckingham Fountain. PC Spinlister. See link above in 'Getting Around' to full description of bike trail

Day 2 - Go outside and play

Activity Suggestions - Try working off last night’s indulgences by touring Millennium Park by bicycle. They are easy to rent at many locations in the city. In the afternoon, appreciate Chicago’s magnificent skyscraping architecture from the river on a Guided Architecture Boat Tour that runs hourly from the Michigan Avenue bridge. Or how about a romantic picnic in the park? In the Summer, many free concerts play from the Millennium Park Pavilion. The grassy fields in front are a perfect place for a champagne spread.

Evening suggestions - No trip to Chicago is complete without a taste of Italian food! Rush Street is famous for its historical restaurants and busy nightlife. If you are looking for a more unique upscale dining experience, try Prosecco in the heart of the River North Gallery District – one of the few places where the chef actively engages with his diners. Or cab over to Monteverde for some Black Truffle Egg Yolk ravioli. If you go to the theatre and still have some energy? Top off your evening with a nightcap and some dessert at the Gilt Bar.

PC - Somerset

Day 3 - Shopping and brunch

Activity suggestions - Not too many places top the shopping on Michigan Avenue! Even if you are simply a window-looker, you will get your exercise walking up and down this designer - lined street. If you don’t speak Dior, you can easily pass time people-watching. But packing a lightweight duffle bag in your suitcase makes for easy carry-on if your credit card does burn a hole in your pocket. Once you have shopped until you dropped, head over to Somerset at the Viceroy for mimosas and brunch.

Have fun!

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