"It is hopeless for the occasional visitor to try to keep up with Chicago. She outgrows his prophecies faster than he can make them." Mark Twain
Chicago, on Lake Michigan in Illinois, is a bustling, dynamic contemporary business center and one of the largest and most cosmopolitan cities in the U.S. Renowned for its bold architecture, the skyline rivals Manhattan with its densely packed skyscrapers; most notably, the iconic John Hancock Center. The city is home to many industries, most notably: auto manufacturing, bio-tech, fintech and food manufacturing.
This business hub promises and delivers first class hotels and dining; endless cultural activities and events; the city is also renowned for its jazz and blues scene.
Getting from the airport to the city centre
Chicago has two major airports: Chicago O'Hare (ORD) is the largest hub of United Airlines and the second-largest hub of American Airlines and the fifth busiest airport in the world.
Chicago Midway (MDW) is more popular with locals and domestic travelers. Both provide easy access into the city, but O'Hare is much larger. For everything you could wish to know about either airport, including transportation options, here.
O'Hare is connected to Chicago by train using the Blue Line of Chicago 'L'. It runs 24 hours a day. The transit time from Central Loop to O'Hare International airport is approximately 40 minutes. Chicago Transit Authority (CTA); MetraRail; and Pace Suburban Bus.
For a personal driver (taxi or limo), check here. A taxi to downtown is approximately $40 one way, plus tip.
Getting Around Chicago
The best way to see Chicago, also known as "The Windy City", is by the "L" train. The "L", as it is called, is actually an elevated train that runs throughout the city. You can buy fare cards and passes from vending machines, online at the Chicago Transit Authority (CTA) website, grocery stores and drugstores throughout the city and suburbs. For full fare information, schedule details, transit card retailers and maps, visit transitchicago.com.
The city of Chicago itself is too big to navigate by bike or foot; however, either mode is ideal for exploring the city's individual neighborhoods and this is something you definitely want to do after your work is done for the day and you are looking for a little local flavor. Chicago is laid out on an easy-to-navigate grid and the city's Divvy bike share system allows you to hop on a bike as needed. Divvy day passes cost $7; learn more and register here.
Local Eateries and Bar Hotspots
Chicago’s Magnificent Mile offers visitors an enticing and delectable selection of places to dine. It’s a literal and figurative melting pot of diverse international cuisine along the 13-block stretch of North Michigan Avenue that runs from the banks of the Chicago River to the south, to Oak Street to the north. Whether you are looking for fresh grilled steaks, organic fare, Indian, American, French, Latin, Asian, Italian, or fresh-caught seafood, you'll find it here. This area is also central to the business district, meaning you can leave your hotel, meet clients for dinner and enjoy evening entertainment, all within a district that extends a full square mile from North Michigan Avenue.
Odyssey Cruises offers an utterly unique experience for visitors to Chicago. If you're looking to impress a new client, try a dinner and dance cruise aboard a yacht while cruising by the downtown skyscrapers twinkling and reflecting in the night sky. You can also book private events with Odyssey.
Blackbird is a west side restaurant that draws the city's power brokers and movers and shakers. James Beard award winning Chef Paul Kahan draws on both local producers and the world for ingredients, meaning an ever changing, seasonal array of appetizers, crisp salads and unique main courses, such as miso-cured pork collar with salsify, black trumpet mushrooms, buckwheat and grapefruit. This spot gets crowded, but it's all part of the energy and vibe. Private dining room for special events accommodates up to 48 diners. Reservations a must.
Located just off Michigan Avenue, Morton's the Steakhouse a is world renowned Chicago-born and -bred steakhouse that demands a reservation and patience in getting that reservation, but proves infinitely worth the wait. Sure, the steaks are to-die-for-delicious, but the chopped salad is also a meal on its own and of course there are seafood options and enough other delicacies to satisfy even the most finicky eater. The establishment features over 4,000 square feet of private dining space in six private dining rooms for client entertainment.
Your after dinner options in this city are staggering. Live theater, Broadway shows, comedy clubs, opera, and ballet are but a few, but most of all, live music that will have you wondering whether you are in the French Quarter in New Orleans, or perhaps New York. Sultry blues bars and sizzling smooth jazz clubs await. You can choose from big name performers, or talented locals, but if you even think you might like jazz and blues, this is the place to try it. Buddy Guy's downtown Legends is gritty and oozing with talent. You may be lucky enough to see him perform live, or meet him at the bar while he oversees his operation.
Kingston Mines, located in Lincoln Park is a club with an unusual setup: two different bands in two different rooms on two different stages, with MC Frank Pellegrino keeping things moving at all times. Wild, fast and fun. This is where to take your client after that serious dinner.
Rosa's Lounge, located in a West Side neighborhood, is family-run, owned by talented local drummer Tony Mangiullo and his mother, after whom the place is named. The schedule mixes local musicians (including a weekly jam) with rising out-of-town acts.
For the Health and Fitness Conscious
Chicago is a fabulous city for walking because there is so much ground to cover and so much to see and do. A Nature Lover's Guide to Lincoln Park is a walk well worth taking. Along Lake Michigan's bucolic shores, green fields are dotted with lagoons, a zoo and conservatory, historic buildings, playgrounds and cultivated gardens with plenty of park snacks available, in addition to local bars and restaurants.
If you want to get your exercise running through the windy city, mapmyrun.com offers hundreds of running routes with maps, elevations and distances, so you can plan, track, analyze and share your journey. Download the free app today!
Let's be frank: You're going to need to buy another suitcase! Shoppers might begin on the Magnificent Mile, the cosmopolitan section of Michigan Avenue that bustles with shopping opportunities from towering shopping centers, trendy designer studios, unique specialty retail shops, iconic department stores, luxurious boutiques and trendy favorites.
Chicago's Loop has been a shopper's paradise for more than a century. Anchored by State Street, located in the heart of downtown, iconic "Great Street," features tremendous variety with designer luxury brands alongside bargain finds. Stroll through the legendary Macy's that's part retail mecca, part history museum.
If you're looking for quality consignment, try eDrop-Off on North Halsted Street for authentic, new, and gently used luxury clothing, shoes, and accessories, as well as one-of-a-kind private collections from high-end brands (such as Chanel). Le Thrift, 1821 West Chicago Avenue, features a mix of contemporary luxury, name-brand, and vintage clothing and accessories. For more consignment stores: Refinery29.
Fancy Something a Bit Different?
There's no question about it: If you have any downtime you must go to the Art Institute. Why? For starters, there are more than 300,000 artworks and artifacts from all over the world and every era from antiquity to the present. Popular pieces include the Japanese prints, fragments of local buildings by Frank Lloyd Wright and the Thorne Miniature Rooms. Renzo Piano’s light-filled Modern Wing will take your breath away and is an idyllic spot to savor the Art Institute’s architecture and design collection, modern and contemporary art, and spectacular views of Millennium Park.
Right, that’s your itinerary covered. Now for all your business hotel booking needs, Roomex has you covered. No costs, no fees, no contracts, it’s a no-brainer. Request a demo to see why it's so popular with Office Managers and Personal Assistants.
Looking for the inside track on all of Europe's highlights? Download our Ultimate European City Guide for Business Travellers below. We've covered all the main business capitals and we're adding a new city every week. If you know someone who travels a lot on business, download it below for free and share it with them!