Chicago, “The Windy City”, is a major hub for finance, industry, telecommunications, commerce and transportation. The Chicago Mercantile Exchange is one of largest financial and commodity derivatives exchanges in the world. The city’s main airport, O’Hare, is the second busiest airport globally and the region also has the largest number of US highways and railroad freight. Its history is rich with luminaries in fields such as architecture, economics, physical sciences, not to mention its fair share of infamous characters. The city’s distinct neighborhoods offer an array of cultural, historical, sporting and entertainment hubs. Our advice is to stay Downtown and plan your hosting activities in the West Loop neighborhoods.


  • VIRGIN HOTEL CHICAGO – Opened as the pilot Virgin Hotel in the US, this spot is everything you’d expect from Virgin: fun, sexy, modern and cool. The hotel bar offers free drinks every night between 7 – 8pm. Virgin Hotel is also a very short walk away from Millennium Park. Our tip: ask for a high-level room as the elevated train line can be noisy at night.
  • THE LANGHAM – Located in the heart of Downtown, close to The Loop, the Langham has elegant rooms, great service and a very funky bar.
  • SOHO HO– USE – Our only pick in the ultra-cool West Loop neighborhood, this is Chicago’s branch of the famously exclusive members’ club and hotel. Our tip: stay and take advantage of guest access to the private members’ club. Sweet talk the host ahead of time and they might give you permission to take guests/clients up to the club.
  • PENINSULA – Set in a landmark high-rise Downtown, this is our pick for the best hotel in Chicago. The swanky rooms have been recently renovated with an emphasis placed on ultra-modern tech features. Dining options include an upscale Chinese eatery, a European-style cafe and a sophisticated cocktail bar.
  • HOTEL LINCOLN – Dating back to the 1920’s, this funky vintage-style hotel is set in the Old Town Triangle off Lincoln Park. It’s a great location for morning runs or evening walks.  The hotel offers plenty of freebies including bike rentals, pedicabs, rooftop yoga classes and a wine hour.
  • THOMPSON CHICAGO – Close to Downtown in the Gold Coast/Magnificent Mile area, this trendy, upscale hotel has a great location and a fabulous restaurant called Nico’s.


  • MATTER – Community of healthcare innovators located in the heart of Downtown/The Loop.
  • 1871  hub for digital startups located in the Merchandise Mart. They provide access to mentors, educational resources and even potential investors
  • WEWORK – A network of four facilities in the Downtown/Loop. Our top pick is the Fulton office located in West Loop due to its close proximity to bars, coffee shops and restaurants.
  • FREE RANGE SPACE – Located 20 minutes from Downtown, this is creative space sits in the up-and-coming residential neighborhood Wicker Park. It is situated on the main thoroughfare on North Avenue (en-route to the airport).



  • FULTON MARKET – A district in the West Loop, these few blocks are packed with fantastic eateries and great coffee shops including one of our favorites, LITTLE GOAT DINER, which offers one of the best breakfast in Chicago. For small meetings and product launches or events, check out their rooftop kitchen.
  • INTELLIGENTSIA – Seriously amazing coffee; this is the good stuff! They have six locations across Chicago, including three in Downtown/Loop: Monadnock, Broadway and Millennium Park.
  • SAWADA COFFEE – Founded by Japanese coffee artist Hiroshi Sawada, a world-renowned latte art competitor, Sawada is located in the Central West Loop.
  • ASADO COFFEE COMPANY – A purist coffee shop with a simple menu. Ideal for those who don’t want to mess around with their coffee. Two central locations: 1432 Irving Park Rd and 363 W. Erie St.
  • WHISPERS – A quaint pit stop offering really good coffee, baked goods and gelato (affogato anyone?). Two locations: 520 N Michigan Ave #2 and 1031 North State St.


  • 3 ARTS CLUB CAFE – Incredible chic setting for lunch or dinner in Old Town, half-way between Downtown and Lincoln Park. Fabulous for business meetings and hosting small events.
  • FIG & OLIVE – Chicago’s branch has a prime location in the super high-end Gold Coast area; same block as Thompson Hotel. Fig & Olive provides an upscale venue for hosting events.
  • NICO OSTERIA – A delightfully authentic osteria featuring Italian seafood specialties, cocktails and wines located in the Thompson Hotel.
  • SUMMER HO– USE – Sunny restaurant serving New American grub in an airy space with an atrium. This place is a slice of California in Chicago.
  • SIGNATURE ROOM – Located on the 95th floor of the John Hancock building, it’s perfect for cocktails at sunset or dinner with the best views in the city!


  • J PARKER – Swanky rooftop lounge in the Hotel Lincoln that offers bespoke Mexican, Cuban and Spanish cocktails, paired with seasonally-influenced New American cuisine.
  • CINDY’S ROOFTOP BAR – Ultra stylish rooftop bar/eatery situated above the Athletic Association Hotel. It has an awesome rooftop restaurant and open-air terrace with panoramic views of Millennium Park, the Art Institute and Lake Michigan.
  • SIXTEEN AT TRUMP HOTEL – The best rooftop bar in Chicago with 360-degree views over the historic buildings of Chicago.
  • THE VIOLET HOUR – An uber cool speakeasy offering creative cocktails and small bites, located in the Wicker Park area, West of Lincoln Park.
  • LONDON HO– USE – A great rooftop with an amazing view of the Chicago River. Reservations highly recommended!


  • Chicago is an amazing summer city; once the sun comes out, the city transforms. Start out with a stroll along the Riverwalk situated along Chicago River. Stop at one of the bars or cafes on the water for lunch or drinks. Kayak rentals are also available – check out URBAN KAYAKS.
  • Walk, run or cycle on the Lakefront path to Shedd Aquarium for incredible views of the city skyline. Our tip is to head to BOBBY’S BIKE HIRE adjacent to Navy Pier and cycle south along the lake through Millennium Park to the aquarium.
  • Another great summer must-do experience is a baseball game at WRIGLEY FIELD. Check out the listings to see if your visit coincides.
  • Chicago has a few architecture boat tours but our local insiders recommend CHICAGO’S FIRST LADY.
  • The J HANCOCK BUILDING offers amazing inner-city skyline views. Our recommendation is to head up to the Signature Lounge for drinks, rather than the observatory.
  • Dinner Reservations: Get friendly with your concierge. Chicago’s best tables often get booked months in advance, but there’s always a last-minute reservation with your name on it if you know the right people.
  • For more information on local events, activities and experiences check out CHICAGO TOURISM.


  • Chicago is incredibly walkable so getting around is easy. The Loop and West Loop are situated south across the River and Downtown is north. For the navigationally-challenged, the lake is always east.
  • West Loop is the trendiest neighborhood for dining and nightlife. However, hotels in this area tend to be lacking in amenity and personality (except for the upscale Soho House). Our suggestion is to choose one of the many Downtown hotels and use it as a base for your exploration.
  • UBERLYFT or local Chicago cabs will see you right through the city. O’Hare is always crazy and traffic into the city can be a nightmare. Those that feel comfortable braving public infrastructure can catch THE BLUE LINE from O’Hare for $2.25.  You’ll be Downtown in 40 minutes. Taxis from the airport can take 25 minutes or two hours depending on the time of day. Don’t rent a car unless you are doing lots of meetings in the north or western suburbs.
  • Like many US cities, Chicago has a crime problem but it’s mostly isolated to specific neighborhoods located west and south of Downtown. The majority of Chicago, and certainly the main business areas, are extremely safe.  Our tip: Avoid evening activities in South Chicago.