After Day 1, you should be familiar with downtown Chicago. Now it's time to explore at least part of the Museum Campus, home to three major museums. Although I recommend the Field Museum for this itinerary, you could certainly substitute the nearby Shedd Aquarium or Adler Planetarium, depending on your interests. The first part of this day keeps you firmly in tourist territory, but you'll journey off the beaten track later in the day when you wander through Wrigleyville and get a sense of how real Chicagoans live.
Start: Bus no. 6, 10, 12, 130, or 146 to Roosevelt Road and Lake Shore Drive.
1. Field Museum of Natural History
You'll feel as though you've entered a truly grand place when you walk into the museum's massive Stanley Field Hall and come face to face with Sue, the largest Tyrannosaurus rex fossil ever discovered. The Field Museum is one of those classic something-for-everyone institutions where you can wander for hours. The Inside Ancient Egypt exhibit is more than just mummies: It's a complete re-creation of ancient daily life, including a marketplace, royal barge, and religious shrines (with lots of hands-on activities for kids). The second-floor African and South Pacific exhibits are also worth a stop, with beautifully designed interactive displays. But the Field also has a certain timeless quality: The old-fashioned animals-of-the-world dioramas, for example, have remained unchanged for decades.
2. Buckingham Fountain
This grand stone fountain is one of the city's iconic structures. (If you're a sitcom fan, you might recognize it from the opening credits of Married with Children.) Try to get here on the hour, when jets of water spurt dramatically into the sky. The fountain blazes with colored lights at night, so if you're staying downtown, it's also worth a stop after dark. (Note: The fountain is closed Nov-Mar.)
3. Lake Michigan or Chicago River cruise
Departing from a dock at the nearby Shedd Aquarium, Shoreline Sightseeing runs water taxis that cruise north to Navy Pier (daily from Memorial Day to Labor Day). From the pier, you can also catch boats that cruise along the Chicago River all the way to the Willis Tower.
4. Navy Pier
Yes, it's touristy and crowded, but Navy Pier is also full of energy — and if you stroll all the way to the end, you'll be rewarded with great views of downtown. If you're traveling with kids, stopping at Navy Pier is pretty much mandatory; it has a carousel and other carnival-type rides, lots of boats to admire, and the Chicago Children's Museum.
5. Wrigley Field
If you're a baseball fan, Wrigley is hallowed ground: the second-oldest stadium in the major leagues, home to the 2016 World Series champs, the Chicago Cubs. The surrounding blocks are a good place to stock up on Cubs souvenirs. If you want to catch a game, tickets can be tough to come by (the entire season tends to be sold out by Opening Day). Show up an hour or so before a game, and you can sometimes find a season ticket holder trying to sell unused seats (and ticket brokers always have seats available — for a price).
If you're not staying for a game and would rather explore a residential neighborhood, walk west on Addison Street for 5 blocks until you get to:
6. Southport Avenue
This area is well into the gentrified stage (witness the number of trendy clothing boutiques), but it's still very much a neighborhood. Wander Southport between Belmont Avenue and Grace Street, and you'll see young moms pushing designer strollers, singles walking their dogs, and hardly any other tourists. If you're here in the early evening, you'll find plenty of low-key, affordable restaurants for dinner. When you're ready to head back downtown, you can hop on the Brown Line at the Southport stop.
7. Julius Meinl
Run by an Austrian coffee company, this cafe is a mix of Old World and New. Large picture windows make it feel bright and inviting, while the European pastries and coffee (served elegantly on silver trays) are a welcome change from standard chain coffeehouses.
8. Buddy Guy's Legends
Chicago is the birthplace of "electric blues," that rocking blend of soulful singing and wailing electric guitars. To experience the city's most famous form of music, head for Buddy Guy's Legends in the South Loop, which has the honky-tonk feel of a Southern roadhouse. The owner, blues guitarist and Rock and Roll Hall of Famer Buddy Guy, makes regular appearances; even if he's not on the bill, the talent level is always top-notch. (If you're staying on the North Side of the city and would rather stick close to home, try Kingston Mines, Blue Chicago, or B.L.U.E.S.)
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.