Chicago

1410 S Museum Campus Dr

Home of the NFL's Chicago Bears, and from 2020 home (again) to Chicago Fire FC of Major League Soccer. If you'd like to see a Bears game, then you have something in common with many Chicagoans; there's no point in listing ticket prices…

Sox-35th Red Line

Formerly known as New Comiskey Park and later as U.S. Cellular Field and Guaranteed Rate Field, this is the home of the White Sox. The stadium itself was a notorious dud when it opened in 1991, but recent renovations have helped…

20 Madison bus· Pricey

Home of the NBA Chicago Bulls and the NHL Chicago Blackhawks. The United Center doesn't have much in the way of character as a stadium, but the sightlines are great from anywhere in the house, and both teams are on an upswing.

Addison Red Line· Cheap

Ernie Banks, Harry Caray, the 1908 champs, and the 2016 champs; yes, this is the home of the Chicago Cubs, the North Side's beloved baseball team.

Adams/Wabash CTA· Moderate

Home of Chicago's renowned orchestra; they spend a lot of time on the road, though, so visiting orchestras and stately jazz concerts can also be found here, as can the occasional curveball like a silent film.

Representing Northwestern University in seven men's and 10 women's sports in the Big Ten Conference. Notably, it's the only Division I school in the immediate Chicago area that plays football for the time being, and even after Chicago…

1122 E 87th St· Cheap

Ok, this place is cool. A roller rink oozing with South Side character and home to not a few serious skaters who flaunt their moves to smooth R&B and old school.

· Expensive

Formerly a traveling tour, Lollapalooza has now found a permanent location in Chicago and grown quite a bit. It's a massive three day collection of popular and lesser-known national and local rock and hip hop bands.

between 500–1550 Lake Shore Dr

There is plenty of everybody doing everything at Oak Street Beach. Beyond swimming and sun-tanning, it's one of the city's most popular spots for beach volleyball, and there are concrete paths for cycling and skating.

3947 S Martin Luther King Jr Dr· Moderate

A great little place serving all sorts of different combinations of, as you might expect, chicken and waffles, as well as your standard soul food menu, expertly executed.

4 E Madison St· Cheap

Whether Garrett's shout-out-loud delicious popcorn is the cap to a good lunch or composes the entire meal is up to you and your conscience. "The Mix" is equal parts caramel- and cheese-coated popcorn; strange as it sounds, the combination…

Damen Blue Line

Named after a line in T.S. Eliot's The Waste Land, The Violet Hour is hidden away — there's no sign, and no name on the door. Inside, though, is a marvelous, decadent, Alice-in-Wonderland plus speakeasy vibe. It's a great place for a date.

65 Grand bus· Moderate

In the pizza wars between Chicago-style, Brooklyn, Naples, and gourmet-trendy, Chicago of course wins. But the pizza wars are truly a fraud, overlooking pizza (more precisely, apizza) from the humbler city of New Haven, which may indeed…

1327 E 57th St· Cheap

An Italian place very popular with the students, that can lay claim to above average baked goods, fine thin-crust pizza, Italian dishes, and a fun ambiance in their downstairs seating area (a separate door to the west of the street-level…

1172 E 55th St· Cheap

From the University perspective, this is the one and only real bar in Hyde Park (and accordingly, the only establishment that was saved from the University-driven "urban removal").

17 E Monroe St· Expensive

With over 1,600 rooms and no shortage of luxuries, the Palmer House is one of Chicago's most memorable hotels. The first Palmer House was built by business magnate Potter Palmer for his socialite wife Bertha.

Library CTA, Jackson Blue Line· Expensive

The Congress Hotel has seen visits from most U.S. presidents since it was built in 1893. Today, other hotels have overtaken the Congress in the glamour class, leaving it behind as a great deal with a colorful past.

Chicago Red Line· Expensive

It was swallowed into the Hilton chain some years ago, but the Drake is still the definition of old Chicago elegance. Founded in 1920, it's on the National Register of Historic Places, and probably has a longer list of celebrity guests…

Damen Blue Line· Expensive

Located in the renovated art-deco 1929 Northwest Tower, hotel features small but comfortable rooms immediately adjacent to the Damen Blue Line stop in the heart Wicker Park.

3111 S Aberdeen St· Expensive

Cozy spacious rooms within an urban Benedictine monastery. The price is way lower than what you would spend in a downtown hotel, but the accommodations actually blow those hotels out of the water (multiple rooms, private gardens!), and the…

Library CTA, Jackson Red Line, LaSalle Blue Line· Cheap

Right in the middle of the downtown college ruckus, HI Chicago is not far from Union and Ogilvie, but will take some navigating from either airport into Chicago. Available 24 hours a day, 365 days a year.