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Aug 3, 2019

Business Travelers' Guide to Chicago Beyond GBTA

Samantha Shankman

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We believe in the power of meeting in-person and that goes far beyond the boardroom or conference center. Business travel means more than shaking hands on important deals — it’s about meeting face-to-face to learn more about clients, partners, and colleagues to form deeper, more authentic relationships. More than 60 TripActions team members are heading out to Chicago this weekend, and we are looking forward to meeting you and enjoying the Windy City during the best month of the year.

Outside of the incredible sessions, panels, and parties planned throughout GBTA, we’re looking forward to preparing for the week ahead with an early Sunday morning river run and cold brews from local coffee shops, as well as dinners out with customers and colleagues.

We spoke to Chicago natives — including our very own Chi-town team — to learn and share the hottest coffee shops, restaurants, outdoor spaces, and attractions to explore outside your hotel and McCormick Place — whether you only have 30 minutes in the morning or an extra day to wind down after the big event concludes.

Coffee Shops

Mojo Coffee

Mojo Coffee is a New Zealand-based coffee shop that makes its coffee extra strong, and holds a strong belief that coffee is only as good as the conversation that happens around it. This location - one of three in Chicago - opened this Spring and was specifically built for a business clientele. And if the hotel buffet just isn’t cutting it, they also offer fresh breakfast items such as avocado toast and shashuka.

Address: 30 N Wabash Street, River North, AMA Plaza Hours: 7 am - 5 pm

The Tiny Tapp Café

The Tiny Tapp Café was made for business travelers who need to clock in a good workout or at least a solid session of “me” time before the day begins. Located directly along the Chicago Riverwalk, you can arrive at 7 am for a strong cold brew and walk along the river while calling clients in Europe or zenning out with a quick session of Headspace.

Address: 55 W. Riverwalk South Hours: 7 am - 10 pm

Intelligentsia Coffee Millennium Park Coffeebar

Intelligentsia is Chicago’s local high end coffee shop. With several locations, you can order a caffeine kick before or after a morning run, enjoy a view of the river, or fuel up for the shuttle ride to McCormick Place.

Address: 53 E Randolph St, Chicago, IL 60601 Hours: 6:30 am - 8 pm


Looking for a more natural morning pick-me-up? HI-VIBE is a superfood juicery with cold-pressed green juices, superfood smoothies, açaí bowls, matcha green tea lattes, and raw snacks. If you’re dealing with tricky food allergies or just can’t shake those post-plane sniffles, this is your spot.

Address: 160 W Kinzie Street Hours: 7 am - 7 pm


City Winery

City Winery — a recreation of its beloved Randolph Street outpost — is one of the best dining options along The Riverwalk. Not only will you find an extensive wine list and menu featuring fresh salads, creative pastas, and meat or cheese spreads, you’ll enjoy a sweet summer breeze with live music in a relaxed atmosphere. Be ready to order from a window and a waiter will deliver to your table.

Bavette’s Steak House

For those looking for the best steak restaurant in Chicago, Bavette’s is a must visit. The stylish dining room sets the mood for a timeless steakhouse dinner including seafood towers, endless side dishes, and house-made desserts. There is a curated international wine list and traditional cocktails to sip to the backdrop of live jazz.

Lou Malnati’s

For those looking to try the world famous Chicago-style deep dish pizza, Lou Malnati's is a must, according to the TripActions Chicago office. There are locations throughout the city and the River North location is a short drive from most business hotels. They open early and don’t close until late. With a warm, wood-paneled dining room, Lou Malnati’s is the spot to go with your closest colleagues after GBTA wraps to celebrate successes from the week over some thick melted cheese.

Pizzeria Portofino

Pizzeria Portofino opened this month as part of the riverwalk’s revival. This multi-level space features a pizzeria and upscale seafood restaurant so the group can choose from hand-stretched pizzas made with stone-ground Midwestern grains or charcoal grilled seafood such as dorade and artichoke or the Seafood Mista. There are also floor-to-ceiling windows providing incredible views no matter the weather. The venue comes from Chicago’s premier dining group Lettuce Entertain You.

Seeking more upscale dinner spots or casual joints? Our Chicago team recommends AlineaAbaThe KitchenThe GageGibsons Italia, or Little Goat Diner.

Happy Hour Spots

Bar Ramone

Bar Ramone is a Spanish wine bar with a curated ever-changing wine list of just 100 bottles and a small plates menu featuring favorites including house-made tomato bread, patatas bravas, mushroom pintxos, and Galacian octopus. The space is intimate, so we recommend Bar Ramone for wow-ing that one special client rather than organizing a group outing here.


It’s worth taking advantage of Chicago’s delightful August weather and visit rooftop and riverside happy hours. Boleo is a chic South American rooftop restaurant and cocktail lounge atop the Kimpton Gray Hotel. Named after a move from the Argentine tango, Boleo pays tribute to its roots with live music every evening starting Tuesday. The menu is tapas-style with plates inspired by Peruvian and Argentine street food. To sip, there is everything from a group punch bowl to Pisco sours as well as more traditional business drinks.

London House Rooftop Bar

With sweeping views of the Chicago River, Lake Michigan, and the Magnificent Mile, London House’s Rooftop Bar is a special spot to enjoy cocktails and Americana cuisine with colleagues or clients. Housed on top the luxury hotel, the location alone adds an air of refinement. Plus, it’s open until midnight.

VU Rooftop Bar

A 10-minute walk from McCormick Place, VU Rooftop Bar is the kind of space that should be mandatory next to every convention center. When the 13,000-square-foot space opened on the 22nd floor, convention attendees gained a new spot for skyline views, small plates and fancy cocktails. An outdoor deck features TVs, fire pits, and seating with everything from a pork belly bar to mushroom tostadas on the menu.


If you have some extra time in the Windy City, or carve some out to make the most of your visit, here are some must-visits to make your stay extra memorable:

The Field Museum of Natural History

Situated a 10-minute drive from the McCormick Center and most business hotels, The Field Museum of Natural History’s proximity to this week’s events belies its significance. Field is one of the largest natural history museums in the country, with exhibitions ranging from the earliest fossils to present-day cultures explored through interactive programming. Looking for something a little lighter?

In August, The Chicago Brewseum is hosting its first Field exhibition — Brewing Up Chicago: How Beer Transformed a City — exploring how beer transformed Chicago from a frontier town to a thriving metropolis through objects, photographs, and personal stories.

Admission costs $24 per person.

Chicago Riverwalk

The Chicago Riverwalk is likely steps away from your hotel and well-worth the visit -- even if it is the only site you mosey to outside of GBTA. Here you can stroll down the open, pedestrian waterfront located on the south bank of the Chicago River in downtown. Constructed in 2001 and revived in 2012, it has become one of the most beloved of spaces in the city.

There are spectacular views of Chicago’s famous buildings plus plenty of stops for a strong coffee in the mornings and a fresh drink in the evenings. It makes for a superb way to start the day or transition between the conference and client dinner.

Shedd Aquarium

A short walk across from the Field is the Shedd Aquarium. Shedd is home today to over 32,000 animals with exhibits ranging from the local Lake Michigan ecosystem to a replica of Amazonian waters. This month’s special exhibit Underwater Beauty showcase species from around the world that embody living art.

Admission costs $19.95 for Chicago residents and $39.95 for visitors.

The Vienna Beef Factory Store

This Chicago hot dog and sausage icon celebrated its 125th anniversary last year. If inclined, you can visit Vienna Beef’s flagship store, cafe, and museum in the Bucktown neighborhood. In the museum, you’ll find vintage equipment, an array of memorabilia, and a gold-plated cocktail frankfurter. In the cafe, you can order a fully loaded dog with kraut, pickles, extra ketchup and crinkle fries. It might just be the team outing you needed.

Address: 2501 N Damen Ave Hours: 8 a.m. - 3 p.m.

Local Transportation

While Chicago boasts a robust public transportation system, our recommended way to get around is with Lyft. Lyft finds you a driver in seconds so you and your employees can arrive at their next meeting or event with limited interruptions and stress.

No plans on Sunday?

Join TripAction’s for the official GBTA Kickoff Party on Sunday, August 4 at the The Godfrey Hotel. From 7:30 - 9:30 pm, we’ll enjoy drinks, appetizers, and good company with our co-sponsors United, Lyft, and Sabre. There’s already a waitlist so join fast!

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