Chicago is a lovely town – I visited in 2006 and liked it, and was pleasantly surprised in 2025 to find it was even more majestic than I remembered. It’s built on a huge scale, and the architecture, interesting multilevel street structure, and river / lake views are impressive. It’s a good city tourism option. Map view here.

What do you do in Chicago? Eat (well) and shop, apparently. I was surprised by the sheer volume of retail. As a tourist, I loved the **architecture boat tour and the Art Institute of Chicago, and took several walks just to see and explore – including the very worthwhile **Chicago Riverwalk. The Field Museum was another highlight (see below) if you have a bit more time.

Hotels:

• *Chicago Marriott Downtown Magnificent Mile is perhaps a little better than the InterContinental – better sized rooms and comfortable beds. Bathrooms ready for a renovation. Fine for work, wouldn’t recommend for tourism.
• I stayed at the *InterContinental Chicago Magnificent Mile, which I wouldn’t recommend for tourist visitors, but was fine for a work conference. Good conference rooms, food wasn’t bad, really lovely swimming pool, good location. Rooms were small, weirdly appointed (two beds – no chair? No shelves or drawers?), and a bit tired.

Sites:

• I don’t really consider Chicago a great place to tour churches, but there are a few rather grand ones, including **Holy Name Cathedral: The mother church of the Archdiocese of Chicago and one of the largest Catholic dioceses in the U.S. It’s massive, Gothic Revival Style, completed in 1875.
• Two blocks away, **St. James Cathedral is the oldest church in the Chicago area of the Anglican Communion and Episcopal tradition, having been founded in 1834 (though mostly destroyed in the Great Chicago Fire and rebuilt). Worth a brief visit to look at the barrel ceiling.
• I liked the **Chicago Architecture Center: they have a 3D model of the city that is regularly updated. The exhibits were quite good (I especially liked the content on new focus on making car-free living possible).
• ***The Field Museum of Natural History deserves recognition as the grandparent of many of the world’s best “stuffed animal museums” – one of the largest natural history museums (and reportedly the inventor of the stuffed animal diorama concept). It’s very impressive, well done for the most part, and very overwhelming in scale – pick your favorite themes and skim the rest.
• *The International Museum of Surgical Science is unfortunately not worthwhile. I love this sort of thing, but it’s a minor collection and very overpriced.
• The **Rookery Building is a historic office building at 209 South LaSalle Street, considered the oldest standing high-rise in Chicago.While the red granite exterior is striking on its own, the renovated interior is notable – the lobby was remodeled between 1905 and 1907 by Frank Lloyd Wright, and Wright assistant William Drummond remodeled the structure further in 1931. It’s a bit over the top for modern tastes (gold and marble and cast iron), but worth a visit. 
• **Tribune Tower: It’s easy to walk quickly past this building, but linger to look at street level – the structure is embedded with over 150 rocks and fragments from world landmarks (the Great Wall of China, the Pyramids, the Parthenon, the Taj Mahal).

Food:

• I went to **Egg Harbor Cafe twice – very good American-style breakfast with all the options you’d expect.
• The **Gage appears to be where you go on a fancy work lunch. I wanted to hate it (kind of did), but my meal was remarkable – fish and chips, with boring sub-par chips, but truly world-class fish.
• *Gibsons Bar & Steakhouse: a classic historic restaurant. It really wasn’t very good, food was very overcooked, I’d avoid.
• **Goddess and the Baker, 44 E Grand: A higher end bakery/coffee shop, with multiple locations. It was pretty good (I had a bagel) but crushingly loud.
• *Su Casa Mexican Restaurant is very run of the mill from a food perspective, but the service is excellent and friendly.
• **theWit Chicago has an impressive rooftop bar/dining area. Our group was a bit too big for the size (150-200 would be a better cap), and the noise was deafening. Otherwise though, it’s a pretty space.
• **Zombie Taco: a bit underwhelming from a setting perspective (to go counter inside a Moxi Hotel), but the food was really good. Tacos, quesadillas.