Travel Reviews, Tips & IdeasYou’re in town for just over a day. When my friends visit Chicago for the first time, I recommend they start with all of the activities along the lake. There’s a lot to do and it’s close together.
If you are going to be in Chicago for a few more days, consider the CityPASS, which gets you reduced admission to several of the attractions I’ll mention. You can also get a Chicago Transit Authority pass for unlimited rides for 1, 3, and 7 days (). Most of my recommendations are easily accesible by public transportation (especially the Red Line and the Michigan Avenue buses).
Day One: Night
There are two hotels, on opposite sides of Michigan Avenue, I recommend to friends. The Drake, a Hilton property, is at the top of Michigan Avenue, overlooking Lakeshore Drive and the Ohio State Beach. It’s iconic script sign is visible for a couple miles as you come down the Lakefront Path or Lakeshore Drive, which takes a turn to the east to go around the hotel.
On South Michigan, near Museum Campus, is the Blackstone Hotel, a Renaissance property. This hotel, largely maintained in its historic context, has the original “smoked-filled room” that selected Warren G. Harding for the Republican nomination in 1920.
Check into your room then find some Chicago deep dish. It’s takes 45 minutes to bake these pies, so you need to show up early for the usual dinner time. Many people know about Pizzeria Uno, but the lines tend to be long there. Pizzeria Due, run by the same people, is just up the street and has shorter lines. The pies there are top rate, but I also like Gino’s East, which has more space, and Giordano’s, which has a fuller menu and several locations. No matter whose pie you choose, your eyes will be bigger than your stomach.
After dinner, catch a show at Second City, where many of the people you know from Saturday Night Live probably got their big break. Get tickets for these cabaret-style shows before you show up in Chicago since they tend to sell out far in advance. On some nights, they have late improv shows after the regular shows.
If you want a late night snack (after deep dish you shouldn’t), try the Billy Goat Tavern, made famous outside of Chicago by a Saturday Night Live skit about “cheeseborger, chips, and Pepsi (no Coke).” It’s oldest location in under the Chicago Tribune building, which you should check out before you go to the lower level for your cheeseborger.
Day Two: Morning
My favorite Chicago breakfast spot is Ann Sather, which has too locations. This Swedish restaurant is known for their ligonberry pancakes and their giant cinnamon rolls, which you’ll want to share. Don’t linger; there’s probably a line out the door and you have a big day.
Museum Campus has some of my favorite attractions, and it’s right on the lake with most things close to each other. The Shedd Aquarium has otters, sharks, and beluga whales. The Field Museum has a replica of the T. Rex “Tyrannosaurus Sue.” They also have my favorite thing in Chicago. Find the Tiffany window in the Gem Room. The Chicago Art Institute has my other favorite things, including the Chagall “American Dream” windows, Wood’s American Gothic, and Hopper’s Nighthawks.
A bit farther south, kids will love the Museum of Science and Industry, where they can walk through the hull of a real Boeing 727 and a World War II U-Boat, the U-505, as well as experience many of the other hands-on exhibits.
If you’re an Illinois resident, check the museum’s websites for special “Resident Days” that have free admission. The days and conditions change throughout the year. Chicago residents can get “Museum Passports” from the Chicago Public Library. That might be handy if you’ve just moved to the city and haven’t explored it yet.
Day Two: Afternoon
Chicago is the “city of big shoulders” where they “use everything but the squeal,” so lunch naturally has to be some sort of encased meat. The Chicago hot dog is a special item: a charred frank on a poppy seed bun topped with mustard, a neon-green relish, peppers, tomatoes, onions, and a pickle spear. Top it off with some celery salt to give it that extra kick. I like Gold Coast Dogs for the classic dog. If you want something a bit more special and are willing to travel, try Hot Doug’s, where Doug himself takes your order for his “artisan encased meats”. On Fridays and Saturdays, he offers duck fat fries. Get there early. Even when it’s freezing outside, there’s a line out the door.
After lunch, it’s time to walk off those calories. Chicago has wonderful outdoor recreational areas, including the Lakefront Path which stretches for 17 miles, from Hollywood Avenue to the South Shore Culture Center. Along the path you’ll find Grant Park, Buckingham Fountain (Clarence Buckingham Fountain), the Museum of Science in Industry, a golf course, and several beaches. Rent bikes or Segways, run, walk, or just sit and watch the lake. Visit the “Bean,” a giant, perfectly smooth steel sculpture officially called “Cloudgate.”
Day Two: Evening
Before dinner, go up to the top of the Hancock Building to have a drink in the Signature Lounge. The drinks are on the pricey side, but you’re really paying for the view, from which you can see all of Chicago. If you time it right, you can be sitting at the window bar as the sun sets and Chicago’s lights start to glow. You can also visit the SkyDeck in the building everyone knows as the Sears Tower.
For dinner, Morton’s Steakhouse is my favorite place for a Chicago dinner. As you walk done the steps to their basement location on State Street, you’ll pass portraits of the mayors of Chicago. I recommend the petit filet, grilled asparagus, and the mac and cheese (ask for it even if it’s not on the menu).
After dinner, catch a show at Steppenwolf Theatre, the company co-founded by Gary Sinise in 1974. You see old and new stage plays. If that’s not your thing, check for something at the Pritzker Pavilion, where you can sit in the outdoor amphitheater or further away on the grass.