Refer to this map:
Chicago is on the west shore of Lake Michigan. Much of the area along the lake is various parks, from Lincoln Park on the North to Millennium and Grant Parks on the south.
The downtown area is mostly high-rise businesses and is comprised of the one square mile of the Loop (so named because it is encircled by the Elevated train tracks). The Loop is bounded on the North and West by the Chicago River. North of the river is the one square mile River North, which is where a lot of the clubs, restaurants and residences are.
The East boundary of the Loop and River North is Michigan Avenue, and the part from the River northward is called the Magnificent Mile, because it’s where all the fancy stores are. This is Tourist Central.
The easiest and cheapest way to get from Orlando to Chicago is Southwest non-stop to Midway. Midway is a bit easier to navigate than O’Hare because it is smaller.
Uber works really well in Chicago, and is really cheap. But if you’re feeling adventurous it’s even cheaper to take the El, which is always $2.50. The El is the train system around Chicago. The different lines have colors. The blue line goes to O’Hare, the Orange line goes to Midway. The red line goes North/South and the Green line goes to the west. (The Red line is actually underground in downtown, like the tube in London.) Nearly everything converges on The Loop.
You buy a card that operates the turnstiles. You can get one and put money on it at major stations. The same card works for the buses. Google or Apple maps work well with the El
From the either airport to downtown is under an hour on the El, sometimes less on Uber (but not always).
Separate from the El is the Metra, the train that runs north to Wisconsin, but is not useful for local transportation.
There are also horse drawn carriages in the tourist area along the Magnificent Mile.
Things to Do
City Pass Chicago
If you plan to do several things, the City Pass combination ticket is the best deal. It includes:
Shedd Aquarium – VIP ENTRY
*Skydeck Chicago – FAST PASS
*The Field Museum – VIP ENTRY
*Museum of Science and Industry – VIP ENTRY OR 360 CHICAGO – EXPRESS ENTRY
*Art Institute of Chicago – FAST PASS OR Adler Planetarium – VIP ENTRY
I put an asterisk on the best choices.
Museum of Science and Industry
This is a great museum in a huge building that is the only survivor from the Chicago 1893 World’s Fair where the original Ferris Wheel debuted. That world’s fair was one square mile, and had 700,000 visitors on its closing day alone!
Must see things at the museum are the Coal Mine ride and the German U-Boat On-Board tour. These have specific admission times you select when you get your tickets. Allow at least 4 hours minimum.
The Art Institute of Chicago
Huge, HUGE art museum with an amazing impressionist collection by Renoir, Monet, Van Goghs, plus A Sunday on La Grande Jatte and Nighthawks. Even if you think you don’t know what those are, you do.
You can not even walk this whole museum in 8 hours, so be selective!
Dinosaurs, and all that natural history stuff. And did I mention DINOSAURS?
Chicago Architecture Foundation River Cruise
There are a number of Chicago River boat tours and even a number that focus on the city’s architecture, but this is the best one, because it has a docent from the Architecture Foundation doing the commentary. Even if you’re not that interested in architecture, it’s a great way to see the city and the river, all the way from Lake Michigan past the Sears Tower.
Chicago Loop Bridges
A retired engineer and bridge enthusiast conducts these very personal walking tours of all the different types of drawbridges along the Chicago River, and you get to go into one of the control towers that is now a museum. This is often a private tour.
If you don’t want to take the tour, you can just visit the museum:
Sears Tower (no one calls it Willis Tower)
Our condo is pretty tall, but this building is more than twice as tall. The tour, displays and glass floor of the skyjack are very popular attractions.
Lincoln Park Zoo
This is quite a pleasant zoo, and it also has a great restaurant in the park nearby, North Pond, which has a Michelin star (reservations essential).
There’s a new Ferris Wheel on the pier that gives quite a view of the skyline and lakeshore. This is also where lake cruises depart from. The dinner cruise is nice although the food is nothing special. During the summer there are Disney-quality fireworks every Wednesday and Saturday.
John Hancock Tower
There a great view here because the building is on the Magnificent mile at the lake shore. However you don’t need to pay for 360 Chicago. You can see the same view by having a drink at the Signature Lounge.
Richard H. Driehaus Museum
This mansion from the guided age is right in River North, and is the best preserved historic home I have ever been in. Elaborate marble, woodwork and tiffany glass look like they were installed yesterday. They host changing exhibits, too. When we went there was a collection of original cartoon artwork from 100 year old issues of Puck magazine.
The opulent Chicago Theatre used to be a movie palace, but now hosts major musical and comedy performers. During the day they offer great tours of the building, with lots of fascinating history.
Randolph Street is Chicago’s theatre district, where many shows open before going to Broadway, and where the touring productions come. The major theaters are the Oriental, the Cadillac, and the Goodman. To the north is Steppenwolf, and on Navy pier is the Shakespeare Theatre. There are also dozens of smaller theatres.
Museum of Broadcast Communications
This conveniently located museum will bring back memories of old TV programs, and has a comprehensive collection of radio history. It’s best for adults; there’s not much of interest for little kids.
Frank Lloyd Wright Home and Studio
About 30 minutes to the west of Chicago is Oak Park, where Frank Lloyd write built his own home and studio. It’s very extensive, and the tour shows how his work evolved over time. Be sure to book your tour in advance. There’s also a walking tour of the homes he designed in the surrounding neighborhood, but since you can’t go in those I would skip it. You can Uber for about $30 each way, or take the Green line and be there in 20 minutes or less.
Mars Cheese Castle
If you’re headed to Wisconsin, there’s no place quite like this.
If you have a car, it’s an hour drive to Indiana Wineries. Butler makes good wine from local grapes, and Shady Creek makes good wine from California grapes. Do not go to Anderson’s Orchards and Winery.
Tastebud Food Tours
A local entrepreneur runs some very good food oriented walking tours. I took one where the guide stayed in character as a socialite from the days of the 1893 World’s Fair. We visited a half dozen historic stops and had foods that were invented there. They also do brewery and distillery tours.
Live Music & Bars
Many, many places up and down Hubbard have live music.
Andy’s Jazz Club
Good food and drinks, $14 or $20 cover for live jazz. Shows at 5pm, 7pm, and 9:30-1am.
This restaurant and live music venue is also really into wine, and serves everything in Riedel stemware. The food is good, and they have different acts every night. During the summer there is also a casual outdoor version right on the Riverwalk.
Untitled Supper Club
500 Scotches, great cocktails, good food, and live music are all on offer in different rooms of this speakeasy-themed restaurant and bar.
Three Dots and a Dash
This is the best Tiki Bar you will ever go to. It’s not really on Clark. Enter the alley on Hubbard and follow the neon light to the door. Reservations essential. Even neater is the tiny Bamboo Room within Three Dots and a Dash. A separate, prepaid reservation is needed here. For fifty dollars you get several custom-made tiki drinks, or can have a rum tasting. Ask to sit at the bar so you can talk with the bartender as he makes your drinks.
Chicago has a dozen Michelin-starred restaurants, but mostly I have ignored those, because they take months of planning to get into. These are some favorites by category.
Things to NOT eat in Chicago:
Deep dish pizza. You can get the same stuff at Giordano’s. When the Chicago magazine ratings come out, none of the top pizzas are deep dish.
Chicago-style hot dogs. It’s nothing special, just on a poppy seed bun with a pickle, tomato, and pepper. There are gourmet dogs in town that are better.
Mexican food. Some people like Rick Bayless’ Michelin-starred Topolobampo, or his adjacent Frontera Grill or Xoco, but I’m not impressed. Chicago really doesn’t have a great Mexican restaurant.
Best Restaurant in Town (and the country) – Oriole
The secret is out (two Michelin stars in the first 7 months) but the best place in town is Oriole. Reservations well in advance are essential. Don’t be alarmed that it looks like a warehouse and you are entering off an alley.
French – Mon Ami Gabi
Traditional French Bistro food, perfectly done.
New American – Cafe des Architects
In the Sofitel. The trick here is to put yourself in Chef’s hands and get the tasting menu. Amazing presentations, great price for the quality. Best to go here on a weeknight when the chef is bored.
Eclectic – Girl and the Goat
Stephanie Izzard’s flagship is always packed, but they hold some tables for people who didn’t get reservations two months in advance. Go at 4pm and have a drink in the bar.
Hamburger – Au Cheval
The most famous hamburger in America is at Au Cheval, but good luck getting in. There are a few spinoffs called Small Cheval that are more accessible. But you can also get Au Cheval’s hamburger at a salad place(!) See below.
Salad – 3 Greens Market
This place has an enormous and fresh collection of salad bars, but they also serve Dillman’s famous pastrami sandwiches from another restaurant’s recipe, and the burger made famous at Au Cheval and voted best in the country. So something for everyone!
Sushi and Cocktails – Kumiko
Created by the folks behind the amazing Oriole, Kumiko was selected by Time magazine as one of the best 200 PLACES in the world–not just restaurants. Craft cocktails and creative Asian food. Best to try to reserve a seat at the bar. Even more exclusive is the downstairs Kikko with an omakase served at a small bar.
Pizza – Coalfire
The best pizza in Chicago is not Chicago Pizza, it’s Coalfire’s Pepperoni & Whipped Ricotta.
If you just want a slice, closer by, you can get one for $4 at Dough Bros.Try the spicy Roland.
Barbecue – Chicago q
Chicago q is not a joint, it’s actually a nice restaurant I’m not a fan of Midwestern barbecue sauces, I like a Southern style, which is more like wha they offer here. Try the barbecue sampler appetizer to see what you like; it comes with four sauces. They also have about 100 whiskeys and bourbons, and tasting flights of the same.
Indian Chinese – Vermillion
This place is marching to their own drummer. It’s gourmet Indian unlike any you’ve had. The service is amiable but very whacked – just hang in there for the food.
Steak – Gibson’s Italia
There is almost a steakhouse in every block of River North. One of the most famous is Gibson’s, but this is a new location with a dramatic view of the river. Despite the name, it’s really about steaks, not Italian food.
Italian – RPM Italian
Run by Lettuce Entertainment, a very successful restaurant operator in Chicago, with dozens of great restaurants. Avoid the Michelin-starred Spiaggia.
Popcorn – Garrett’s
Famous for its Chicago Mix, which is half caramel popcorn, half cheddar cheese popcorn. It’s better than it sounds. There’s always a line, but it moves fairly fast.The one on Randolph in the Loop doesn’t usually have a lone.
Donuts – Stan’s
Chicago has some great donut places – Glazed & Infused, Do-Rite Donuts, and Firecakes. But my favorite is Stan’s (six locations), an import from Westwood Village in Los Angeles. You want an old fashioned buttermilk. (At Glazed and Infused you want a maple bacon; you enter through the Davanti Enoteca restaurant.)
Best Hotels in Chicago
Convenient Moderate Hotels
The Chicago Marriott Downtown Magnificent Mile
Convenient Cheap Hotels
Hilton Garden Inn