Dakota's 2025 Guide: Where to Stay, Meet, and Eat in Chicago

Dakota Recommends: Where to Stay, Meet, and Eat in Chicago

Dakota Recommends: Where to Stay, Meet, and Eat in Chicago
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Whether you’re traveling for a conference, meetings, or a quick overnight trip, having reliable go-to spots in a city can make all the difference.

At Dakota, we’ve spent years on the road meeting with allocators, industry professionals, and investment managers across the country and around the world. Along the way, we’ve learned firsthand which hotels, restaurants, and coffee shops consistently deliver. The ones that turn a business trip into a productive, enjoyable experience.

That’s why we created Dakota Recommends. The insider list for business travel exclusive to Dakota Marketplace Members, or with a subscription. 

Built by executive business travelers for executive business travel, it’s a curated collection of hotels, restaurants, coffee shops, and event spaces designed for professionals who expect more from every trip. 

Unlike tourist guides, it’s built for business. Every spot is Dakota Verified, tested by the same team behind Dakota Marketplace and trusted by thousands of firms.

Now live inside Dakota Marketplace, Dakota Recommends includes more than 1,000 verified locations across 25+ U.S. cities, London, and Paris. Each listing features “Dakota Must Trys”... our insider dishes and experiences our team swears by.

Chicago

Chicago has the second most accounts Marketplace. It is one of the most important cities for a sales professional to frequent when targeting any channel.

Chicago is a major consultant hub is the base for Mercer, Fiducient, Marquette Assoc. and AON. These firms have key research contacts here and in other major cities. This Metro Area is also host to 7 Graystone Consulting Teams.

Where Chicago stands out, is its concentration of massive MFOs/RIAs including William Blair, Mesirow Financial, Crescent Grove, Greshem, and Calamos. Two other RIAs to follow are Cresset Wealth and MainStreet Advisors. Both are growing quickly through expansion and acquisition. In total, there are over 110 qualified MFOs/RIAs ready for you to meet with in Marketplace.

For the Banks and Broker-Dealers, Morningstar Investment Management is a must-see, as well as the research folks at CIBC. They are plenty of individual Broker-Dealer Teams, including Matt Morris, a key influencer within UBS.

That’s why we’ve expanded Dakota Recommends here. To help our members navigate the city with the same level of precision they bring to their meetings.

Here’s what’s new inside Dakota Marketplace:

  • 6 Hotels across downtown Chicago balancing comfort, proximity, and convenience
  • 28 Restaurants perfect for client dinners, networking events, and post-meeting meals
  • 7 Coffee Shops ideal for morning meetups or quiet working sessions
  • 6 Event Venues suited for investor receptions, private dinners, and networking events

Every spot meets the Dakota standard: Elevated, professional, travel-tested, and never crowdsourced. These are the same venues our team uses when hosting events, meeting allocators, and building relationships in Chicago.

Dakota Recommends

Dakota Recommends isn’t just a list, it’s a toolkit for business travelers. These are the places that have helped us at Dakota deliver successful meetings, memorable events, and efficient trips time and time again.

When you're traveling for work, trust the spots we've already vetted. You’ll find them all in Dakota Marketplace, organized by metro area, ready to support your goals on the road. We've also incorporated "Dakota Must Trys" under each place listed!

Whether you're planning your next trip or refining your meeting strategy, book a demo of Dakota Marketplace to explore the people and places that keep our team coming back.

MP CTA 9/8/25

Written By: Morgan Holycross, Marketing Manager

Morgan Holycross is a Marketing Manager at Dakota.