Whenever I am asked what my favorite city in the U.S. is, I never hesitate to say Chicago. To me, this city has everything I could possibly want: world-class museums, a great transportation network, one of the best and most efficient airports in the world (and Midway), the friendliest people anywhere in this hemisphere, stunning architecture, amazing food (deep-dish pizza rules), and a very central location with some of the best hotel products to be found. I recently did site inspections at five Chicago hotels. Obviously, there are hundreds more to consider, but hopefully sharing my travels to these five products will give you a feel for some of the best the city has to offer.

Historic hotels are one of my favorite things ever, and Hilton runs two of the finest in the world about six blocks from one another in Chicago. The 1,544-room Hilton Chicago takes up an entire city block on Michigan Avenue, right across from Grant Park. It recently completed a full renovation and looks stunning. The rooms are fresh and all of the public space has been updated. The 280,000 square feet of meeting space flows wonderfully, a rarity in historic hotels.

On the second level, the Grand Ballroom, one of the coolest rooms in the whole city, is a bit over 12,000 square feet of historic elegance. On the same level, you’ll find the International Ballroom, a 22,000-square-foot space, and a large prefunction space, the Normandie Lounge, overlooking the hotel’s spacious entry way. The third and fourth floors have 28 breakout rooms. On the lobby level you add a 10,000-square-foot ballroom, and one level below are spaces that are 40,000, 15,000, 29,000, and 34,000 square feet. The possibilities are truly endless.

A few blocks north, the 1,642-room Palmer House Hilton gets my vote for best lobby in the history of hotels. As you walk in, your neck automatically cranes up, to gawk at the grandeur of the ceiling frescos, before you even notice you’re standing next to handmade gold Tiffany candelabras. Palmer House is the longest continuously operating hotel in the U.S., so it has hospitality down to a science. Little touches like decorating temporary walls to look like Santa’s workshop give you confidence that the team knows how to flawlessly execute any event. The property has over 130,000 square feet of meeting space on multiple levels. My favorite rooms are, not surprisingly, the two most historic and beautiful: the Empire Room off the lobby—5,400 square feet of impeccable elegance—and the Red Lacquer Room, a 7,100-square-foot work of art on the fourth floor. If I were planning a gala or wedding, these rooms would get my instant recommendation. The whole hotel recently underwent a full renovation, and really looks crisp and well maintained. It is well located in the theater district, just a block from the theater playing “Hamilton.” (I saw the show and would recommend it without equivocation to everyone. My expectations were lofty, and they were blown away.)

North of the Chicago River is the beautiful, modern, and impressive Waldorf Astoria Chicago. Wow, this is a hotel I would book without a second’s hesitation. It has 216 rooms, with one of the highest percentages of suites I have seen in a hotel of this size. This hotel is the most luxurious in Chicago, and is a top contender for that title worldwide was well. The spa was large and spacious. Groups of 50–80 people would be great at this hotel, as the largest meeting space is 2,300 square feet. Depending on the time of year, I would suggest an outside reception in the opulent courtyard, something very few other downtown hotels offer.

Also on the Gold Coast is a small boutique hotel perfect for groups up to about 100 or so, Thompson Chicago. I really liked this hotel, and the staff was warm and hospitable. It has 247 rooms, and about 10,000 square feet of meeting space, although the largest is a little over 3,000 square feet. The décor is eclectic and whimsical, and the location of the hotel cannot be beat. All rooms have a water view or a glittering city view. Now a part of Destination Hotels, the Thompson brand is a perfect one for high-end guests wanting more individual attention. The Gold Coast area is one of the most convenient downtown neighborhoods for a visit to Wrigley Field, a summertime activity everyone should do at least once in their lifetime.

The last hotel I saw in my whirlwind trip to the Windy City was the Hyatt Regency at McCormick Place. Larry Panno gave me a tour of the 1,258-room hotel, its 43,000 square feet of onsite meeting space, and the wonderfully flexible attached McCormick Place. We did the tour on motorized scooters, a first for me, and got through all 2.6 million square feet of the center in no time flat.

When I say it is a flexible campus, I truly mean it. You can do one contract to confirm guest rooms, meeting space, theater, exhibition space, and food and beverage. In many cities, this would be four of five contracts. In many cases, a simple room rebate would take care of all of your convention center costs. Because of the huge amount of space under one roof, they can be very flexible with space intensive groups, especially short term. The F&B pricing at the convention center is offered to groups basically at cost, which means your group saves 30 percent over just about any convention center or hotel in the U.S. On a large program, this can be a significant savings.

McCormick Place is huge but has a very tight foot print, and very few meeting spaces are more than a few hundred steps to the hotel. Compared to Las Vegas hotels, or linear convention centers like those in New Orleans, New York City, or Orlando, McCormick Place was incredibly easy and quick to navigate.

The transition between hotel and convention center was seamless. There is now a CTA green line stop just a few blocks away from the center, and a red line stop just a couple of blocks farther. Within the next year or so, several large restaurant concepts will be opening up next to the center. So your attendees have easy transportation options to downtown Chicago, but ample dining choices at the hotel and surrounding area. Also in the next year, the Marriott Marquis, a 1,205-room hotel will open up in the area. It will be attached to one building, but the Hyatt will continue to have the best location at the center of the campus.

As I mentioned, I love Chicago. Easily accessible from anywhere in the U.S. or international gateway city, you will not find a better city in which to do business or that offers your attendees more to do. I have been here over 20 times and my to do list of things I want to do and see in this City of the Big Shoulders is still a mile long.