Destination Guide | Chicago, IL

City Guide

Chicago

Chicago is a well-connected meeting destination, offering easy access through O’Hare and Midway airports and a compact downtown that keeps logistics manageable. While many groups stay close to the Loop, attendees can also explore neighborhoods like the West Loop, River North, Fulton Market, Wicker Park, Logan Square, and Bucktown — each offering a different feel.

The city combines iconic architecture, lakefront views, reliable transit, and a strong dining scene, giving planners plenty of options for corporate meetings, leadership gatherings, dinners, and offsite activities.

Seasonal forecast

Spring

Best window

Mild temps, but often windy

Weather shifts quickly, especially near the lakefront.

Summer

Warm, busy festival season

Peak tourism increases pricing and limits availability.

Fall

Crisp temps, lots of convention activity

Great weather but crowded in September-October.

Winter

Very cold, snowy, and windy

Anticipate delays due to dreary weather.

Transportation options

ORD (O’Hare International Airport)

Chicago’s primary airport with extensive domestic and international flight access.

MDW (Midway International Airport)

Smaller and closer to downtown, often convenient for domestic travelers.

CTA trains

Reliable and cost-effective, with direct rail service connecting both airports to downtown Chicago.

Rideshare & taxis

Widely available, though traffic can significantly impact travel times during peak hours and major events.

Metra & Amtrak

Useful regional rail options for attendees traveling from surrounding Midwest cities and suburbs.

Walkability

Downtown Chicago, River North, West Loop, and the Loop are highly walkable, but plan for less walking during winter visits.

Accommodations

4.7

Boutique hotel

Omni Chicago Hotel

Located on the Magnificent Mile, Omni Chicago is the only hotel on Michigan Avenue with a rooftop space and is well-suited for executives. Its suite-style accommodations and polished atmosphere make it a strong option for leadership stays and business travel.

TROOP PICK

4.6

Hotel

The Emily Hotel

The Emily offers a more modern stay surrounded by some of Chicago’s best restaurants, bars, and creative spaces. The neighborhood has become one of the city’s most revitalized areas while still staying close to the Loop and downtown business districts.

4.5

Unique hotel

Chicago Athletic Association

Set inside a landmark historic building overlooking Millennium Park, the Chicago Athletic Association combines rich local history with a classic downtown Chicago feel. The hotel is also home to Cindy’s Rooftop, a popular spot for skyline views, group dinners, and networking.

Meeting spaces

4.6

Hotel

Pendry Chicago

Pendry Chicago offers modern meeting rooms and a central location near the Riverwalk, Millennium Park, and major downtown hotels.

4.7

Co-working space

Industrious Fulton Market

Industrious has flexible meeting rooms surrounded by restaurants, hotels, and Chicago’s growing tech and business scene. Its modern setup works well for hybrid teams, team workshops, and collaborative meetings.

4.7

Unique venue

LondonHouse Chicago Rooftop

Overlooking the Chicago River and skyline, LondonHouse is a historic building with iconic city views that create a distinctly Chicago experience that feels polished without requiring a large-scale event setup.

Restaurants

The Loyalist

$ - $$

Widely known for serving one of the best burgers in Chicago, this spot also offers a variety of comfort food in a more intimate setting. It’s a great choice for smaller team dinners or relaxed client meals that still feel distinctly local.

Pizzeria Portofino

$$–$$$

Pizzeria Portofino combines wood-fired pizzas and riverfront views in one of the city’s most popular dining spots. The lively outdoor atmosphere makes it a good fit for networking dinners and team gatherings, though reservations can be difficult during the summer.

Girl & the Goat

$$ - $$$

Led by world-renowned chef and Iron Chef winner Stephanie Izard, Girl & the Goat is considered one of Chicago’s most iconic restaurants. The menu is built around bold, shareable dishes — including the restaurant’s signature Pig Face — making it well-suited for group dining. If reservations are limited, Izard’s nearby restaurant Duck Duck Goat is another great option.

Activities

Second City comedy show

Second City is a more casual evening activity that’s well-connected to Chicago’s improv and comedy scene. A great fit for networking, team bonding, or a post-meeting activity.

Architecture boat tour

A river architecture cruise is one of Chicago’s most iconic experiences, with skyline views and local history right on the water. It’s also consistently ranked as one of the top travel experiences in the world.

Jazz & blues clubs

Chicago is known for its historic jazz and blues scene. Andy’s Jazz Club offers live local jazz performances alongside dinner service, while Buddy Guy’s Legends is one of the city’s most iconic spots for classic Chicago blues.