Chicago Attractions Guide


Photos by Cheryl Landes

Editor’s note: I wrote the original Chicago Attractions Guide for a conference that was held in downtown Chicago. After the conference ended and the information was no longer available online, I decided to post the guide on my blog. If you have any other recommendations for places to go and things to do in Chicago, please post them in the comments section. Thanks!

Hours and prices are subject to change.

Outstanding views, friendly people, art and culture, some of the world’s best jazz and blues, and vast green spaces—Chicago has it all. Here are just a few of the highlights.

City Views

360 Chicago Observation Deck at the John Hancock Tower, 875 N Michigan Avenue, (888) 875-8439,

This 360-degree observation deck is on the 94th floor of the John Hancock Tower, 1,000 feet above the Magnificent Mile, where you’ll enjoy incredible views of the Chicago skyline and Lake Michigan. And if you’re in for the thrill of a lifetime, hop aboard the TILT. It’s an enclosed moving platform that literally tilts you out over Michigan Avenue from the 94th floor.

Food is available at the Bar and Café, where you can relax after your TILT ride (if you dare to go).

Hours: 9 a.m.-11 p.m. daily; last entry 30 minutes before closing

City lights view from Chicago 360

Skydeck at the Willis Tower, 233 S Wacker Drive,

Formerly the Sears Tower and the tallest building in the Western Hemisphere (the new One World Trade Center in New York City now takes top honors), the view of Chicago from the 103rd floor is still as amazing as ever. A unique feature of the Skydeck (as if the view of Chicago isn’t unique enough) is that you can walk approximately four feet outside the building for an even more exhilarating bird’s-eye view. It’s called The Ledge and consists of four large glass boxes extending from the Skydeck. Even the floor is glass, so if you look down, you really feel like you’re suspended in air.

Three dining options are available at Skydeck: Breakfast in the Sky, Lunch On 99, and Pie In The Sky. All are expensive: $250 for two for breakfast, $160 for two for lunch, and $200 for two for dinner. If you decide to splurge, make reservations now, because all three restaurants are mostly booked during the IA Summit.

Hours: 9 a.m.-10 p.m. daily; last entry 30 minutes before closing

View from Skydeck at Willis Tower

Music and Other Entertainment

Andy’s Jazz Club & Restaurant, 11 E Hubbard Street, (312) 642-6805,

At least two shows are held nightly at this jazz club/restaurant. Tables are reserved to parties who order dinner; everyone else is seated at the bar. Dinner reservations strongly recommended. Parties with people under 21 are allowed for the 5 p.m. and 7 p.m. shows, but reservations are required, and no entry is allowed after 6:45 p.m. Check the calendar and make reservations online.

Hours: 4:30 p.m.-1 a.m. daily. Dining ends at 11:30 p.m.

Blue Chicago, 536 N Clark Street, (312) 661-0100,

Blue Chicago has live blues music seven nights a week. Drinks are available but no food.

Admission is $10 per person Sunday-Thursday and $12 per person Friday-Saturday. Only ages 21 and older are admitted with valid ID. Pay at the door starting at 8 p.m.

Hours: 8 p.m.-1:30 a.m. Sunday-Friday, 8 p.m.-2:30 a.m. Saturday

B.L.U.E.S., 2519 N Halsted Street, (773) 528-1012,

If you’re looking for a relaxed, friendly atmosphere where you can hear some talented local blues musicians and vocalists, B.L.U.E.S. is the place to go on Chicago’s North Side. This intimate venue allows you see the musicians up close.

Live music is scheduled six nights a week. Drinks are available but no food.

Admission prices vary. Pay at the door. Only ages 21 and older are admitted with valid ID.

Hours: 8 p.m.-2 a.m. Tuesday-Sunday

Buddy Guy’s Legends, 700 S Wabash, (312) 427-1190,

Buddy Guy’s Legends is a “Chicago institution” just around the corner from the hotel. It’s a great place to get a taste of Chicago’s blues culture. A combination blues club/restaurant serving lunch and dinner, Buddy Guy’s features Louisiana-style Cajun and soul food, such as gumbo, jambalaya, chicken and ribs, and catfish po’boys. There’s also a wide selection of burgers, sandwiches, salads, and comfort food. It’s a nice place for happy hour, and usually there’s a free show around 5 p.m. before the main act.

Hours: 5 p.m.-2 a.m. Monday-Tuesday, 11 a.m.-2 a.m. Wednesday-Friday, noon-3 a.m. Saturday, and noon-2 a.m. Sunday

The stage at Buddy Guy’s Legends

Green Mill Jazz Club, 4802 N Broadway Avenue, (773) 878-5552,

If you’re a night owl who loves jazz from the 1930s and 1940s, this is the place for you. The club is modeled after Clark Monroe’s Uptown House in Harlem as it was during the 1940s. Shows are scheduled nightly, and the number of shows vary each night. More shows are scheduled later in the week and on weekends.

Cover charges range from $4 to $15, depending on the band. Seating is first-come, first-served, and the club accepts cash only. An ATM is onsite.

No food is served—drinks only. Ages 21 and older are permitted.

Jazz Showcase, 806 S Plymouth Court at Dearborn Station, (312) 360 0234,

Joe Segal founded the Jazz Showcase in 1947, and at age 91, he’s still welcoming guests to Chicago’s Historic Jazz Listening Room. So many top jazz artists have performed here, including Dizzy Gillespie, Ernestine Anderson, Count Basie, and George Benson. Shows are scheduled nightly, and there’s a special Sunday Matinee for families at 4 p.m., where admission is free for ages 12 and younger.

Check the schedule and buy tickets online. Cash only is accepted at the door, if you don’t buy tickets online, but you can use your credit or debit card for bar service.

Hours: Shows daily at 8 p.m. and 10 p.m. Sunday Matinee at 4 p.m.

The stage at Jazz Showcase

Kingston Mines, 2548 N Halsted Street, (773) 477-4646,

Kingston Mines, founded in 1968, is Chicago’s oldest and longest continuously operating blues club. Live bands play every night on two stages. Doc’s Rib Joint dishes up Southern style food, including Po’ Boys, catfish, fried okra, Cajun red beans and rice, and BBQ.

The cover charge is $12 per person Sunday-Thursday and $15 per person Friday-Saturday.

Hours: 7:30 p.m.-4 a.m. Monday-Thursday, 7 p.m.-4 a.m. Friday, 7 p.m.-5 a.m. Saturday, 6 p.m.-4 a.m. Sunday

M Lounge, 1520 S Wabash Avenue, (312) 447-0201,

This candlelit lounge with luxurious leather and suede seating on Chicago’s South Loop features a lengthy martini and fine spirits list, along with non-alcoholic drinks and coffee. There’s free live music on Tuesday and Wednesday. A DJ plays a variety of music on Friday and Saturday.

Reservations are recommended and can be booked online.

Hours: 6 p.m.-1 a.m. Tuesday-Wednesday, 6 p.m.-2 a.m. Friday, 7 p.m.-3 a.m. Saturday

Rosa’s Lounge, 3420 W Armitage Avenue, (773) 342-0452,

Rosa’s is known as Chicago’s Friendliest Blues Lounge. Tony Mangiullo founded the lounge in 1984, six years after he immigrated from Italy to Chicago to pursue a career as a blues drummer after meeting Jr. Wells and Buddy Guy at a festival in Milan. He named the lounge after his mother, Rosa, who followed him to Chicago to help. Rosa’s has a traditional blues club environment, where talented performers sing traditional and modern blues five nights a week. Food is available, but it’s delivered by local partners.

Ticket prices vary by show and are available online. Ages 21 and older only are admitted.

Hours: 8 p.m.-2 a.m. Tuesday-Friday, 8 p.m.-3 a.m. Saturday

Second City, see locations below, (312) 337-3992,

If you love comedy and improv, Second City is the place to go for some serious laughs and surprises. With seven venues at three locations to choose from, you’ll find something that’s guaranteed to tickle your funny bone. Tickets available online.


  • Chicago Mainstage—1616 N Wells Street
  • t.c. Theater—1608 N Wells Street
  • UP Comedy Club, Donny’s Skybox Theatre, de Maat Studio Theatre, Judy’s Beat Lounge, and The Blackout Cabaret, 230 W North Avenue

Untitled Supper Club, 111 W Kinzie Street, (312) 880-1511,

The Untitled Supper Club features creative American food, whiskey, and craft cocktails in a speakeasy vibe. Menu selections include meat and cheese boards, small plates and shared entrees, seafood, and desserts. There’s no cover charge for live music, but reservations are required and can be booked at Untitled Supper Club’s website.

Hours: 4:30 p.m.-1 a.m. Monday-Tuesday, 4:30 p.m.-2 a.m. Wednesday-Friday, 4:30 p.m.-3 a.m. Saturday

Uptown Underground, 4707 N Broadway Street,

Uptown Underground is a funky nightclub featuring cabaret, burlesque, magic, and variety entertainers. Ages 21 and older only. Ticket prices vary by show. Check the website for the schedule and to buy tickets.

Winter’s Jazz Club, 465 N McClurg Court on the Promenade,

One of the newer jazz clubs in Chicago, Winter’s Jazz Club attracts talented artists in an intimate atmosphere near the Navy Pier. Ticket prices vary by show, and there’s a minimum drink order per person during each show. Check the website for the schedule and to buy tickets. All seating is first-come, first-served. Because seating is limited, buying tickets online in advance ensures you have a seat.

Ages 12-20 are allowed in the listening room but must be accompanied by a parent or guardian.

Hours: 5:30-11 p.m. Tuesday-Saturday, 4-9:30 p.m. Sunday

The stage at Winter’s Jazz Club

Museums and Culture

Adler Planetarium, 1300 S Lake Shore Drive, (312) 922-7827,

The Adler Planetarium opened in 1930 and is the oldest planetarium in the Western Hemisphere.

Hours: 9:30 a.m.-4 p.m. daily

Adler Planetarium

American Writers Museum, 180 N Michigan Avenue, Second Floor, (313) 374-8790,

Inspired by the Dublin Writers Museum in Ireland, the American Writers Museum opened in May 2017 and is the newest museum in Chicago. The museum celebrates the enduring influence of American writers on our history, our identity, our culture, and our daily lives.

Hours: 10 a.m.-5 p.m. Tuesday-Wednesday and Friday-Saturday, and 10 a.m.-6 p.m. Thursday

Art Institute of Chicago, 11 S Michigan Avenue, (312) 443-3600,

More than 300,000 works of art, from ancient to modern, are housed in eight buildings. Also hosts gallery talks, lectures, performances, and other special events throughout the year. Tickets available online or at the institute.

Hours: 10:30 a.m.-5:30 p.m. Monday-Wednesday and Friday-Sunday, 10:30 a.m.-8 p.m. Thursday

Art Institute of Chicago

Chicago Cultural Center, 78 E Washington Street, (312) 744-3316,

Built in 1897 as Chicago’s first central public library, the Chicago Cultural Center is one of the most visited attractions in the city. The south side of the building has the world’s largest stained-glass Tiffany dome, which is 38 feet in diameter and contains 300,000 pieces of glass. On the north side, there’s a 40-foot-diameter stained-glass dome designed by Healy & Millet.

Free special events, including music, theater, dance, films, lectures, art exhibitions, and family activities are held regularly at the center.

Hours: 10 a.m.-7 p.m. Monday-Friday, 10 a.m.-5 p.m. Saturday-Sunday

Chicago Design Museum, 108 N State Street at Block Thirty Seven, Third Floor, (312) 894-6263,

The museum’s mission is to strengthen design culture and build community by facilitating knowledge exchanges through dynamic experiences.

Hours: noon-7 p.m. Tuesday-Saturday

Chicago History Museum, 1601 N Clark Street, (312) 642-4600,

Founded in 1856, the Chicago History Museum is the city’s oldest cultural institution and home to millions of historical objects, images, and documents.

Hours: 9:30 a.m.-4:30 p.m. Monday and Wednesday-Saturday, 9:30 a.m.-9 p.m. Tuesday, and noon-5 p.m. Sunday

Chinatown, (312) 326 5320,

Chicago’s Chinatown is located on the South Side, centered on W Cermak Road and S Wentworth Avenue. Here you’ll find Asian food, museums, and shopping at its best.

The Field Museum, 1400 S Lake Shore Drive, (312) 443-3600,

Founded as the Columbian Museum of Chicago in 1893, The Field Museum inspires curiosity about life on Earth. There’s a lot to see and do here. You can go through this natural history museum in a day, but I don’t recommend it. (I tried it during my first visit.) If you go and have limited time, pick the exhibits you’re most interested in and focus on those first. Then go back and see anything else that fits into your schedule.

Hours: 9 a.m.-5 p.m. daily, except Christmas

The Field Museum in Chicago

Gene Siskel Film Center, 164 N State Street, (312) 846-2800,

Named after nationally renowned film critic Gene Siskel, this film center at the School of the Art Institute of Chicago and features a wide range of films from around the world.

Intuit: The Center for Intuitive and Outsider Art, 756 N Milwaukee Avenue, (312) 243-9088,

Intuit focuses on self-taught art, where the artists show little influence from the mainstream art world. Instead, they’re motivated by their unique personal visions.

Hours: 11 a.m.-6 p.m. Tuesday-Wednesday and Friday, 11 a.m.-7 p.m. Thursday, and noon-5 p.m. Sunday. The museum is closed on Monday, except for school holidays, when it’s open noon-5 p.m.

LEGOLAND Discovery Center, 601 N Martingale Road, Schaumburg, IL, (847) 592-9700,

Kids of all ages will have a blast here. Ten LEGO build and play zones, two rides, and a 4D cinema are only the beginnings of the fun here. Buy tickets online or at the door.

Hours: 10 a.m.-7 p.m. daily. Last entry at 5 p.m.

Museum of Contemporary Art, 220 E Chicago Avenue, (312) 280-2600,

The Museum of Contemporary Art’s collection consists of more than 2,500 works spanning media and movements from the 1920s to the present. Relax and dine or sip a cup of coffee at the Marisol restaurant at the museum. Or grab a drink at the bar.


  • Museum—10 a.m.-9 p.m. Tuesday and Friday, 10 a.m.-5 p.m. Wednesday-Thursday, 10 a.m.-5 p.m. Saturday-Sunday
  • Restaurant—11:30 a.m.-2 p.m. and 5:30-10 p.m. Tuesday-Friday, 10:30 a.m.-2:30 p.m. and 5:30-10 p.m. Saturday, and 10 a.m.-2:30 p.m. Sunday
  • Bar—11:30 a.m.-10 p.m. Tuesday-Thursday, 11:30 a.m.-11 p.m. Friday, 10 a.m.-11 p.m. Saturday, 10 a.m.-2:30 p.m. Sunday
  • Counter Service—8 a.m.-8 p.m. Tuesday and Friday, and 8 a.m.-5 p.m. Wednesday-Thursday and Saturday-Sunday

Museum of Science and Industry, 5700 S Lake Shore Drive, (773) 684-1414,

Chicago’s Museum of Science and Industry is the largest science museum in the Western Hemisphere. Interactive exhibits and hands-on activities explore the world of science and technology. Recent exhibits include an interactive submarine tour, a film expedition through the Amazon forest, structures built from LEGO blocks, and a mirror maze. Buy tickets online, by phone, or at the museum ticket counters.

Hours: 9:30 a.m.-5:30 p.m. daily through March 30 and 9:30 a.m.-9 p.m. March 31

Roger Brown Study Collection, 1926 N Halsted Street, (773) 929-2452,

Roger Brown graduated with his Bachelor’s in Fine Arts from the School of the Art Institute of Chicago (SAIC) in 1970, and shortly thereafter, embarked on a remarkable career as an artist. He created paintings, sculpture, prints, sets and costumes for theatre and opera, and large-scale murals for architectural settings. He is also well-known for his home, studio, and garden settings.

When Brown died, he gave three homes and collections to the SAIC and all of his unsold paintings. One of the three homes is in Chicago, and the collection there is open for tours by appointment.

Shedd Aquarium, 1200 S Lake Shore Drive, (312) 939-2438,

When Shedd Aquarium opened in 1930, it was the largest indoor aquarium in the world. It’s also the first inland aquarium with a permanent saltwater fish collection. It contains 32,000 animals from around the globe, including sea otters, dolphins, and penguins. Tickets available online or at the aquarium.

Hours: 9 a.m.-5 p.m. Monday-Friday and 9 a.m.-6 p.m. Saturday-Sunday

Red sea urchin at the Shedd Aquarium

Tours and Cruises

Chicago Architecture Foundation River Cruise Aboard Chicago’s First Lady, (312) 922-3432,

These tours are seasonal and start on March 31, so I included this one in case anyone is staying longer, or residents are interested. During this 90-minute cruise along the Chicago River, your tour guide will share the story of how Chicago grew from a small settlement to one of the world’s largest cities in less than 100 years. Along the way, the guide also points out more than 50 buildings and talks about their architectural qualities and history.

Tours depart at 10 a.m., noon, 2 p.m., and 4 p.m.

Meet for the tour at the southeast corner of the Michigan Avenue Bridge (now known as the DuSable Bridge) at Wacker Drive. Look for the Chicago Architecture Foundation’s blue awning that marks the entrance to the stairway to the boat. To get directions, enter 112 E. Wacker Drive into your GPS.,, locations vary

This company offers a variety of guided tours: walking historical and architectural tours, city view tours by helicopter, packages to see shows like the Blue Man Group, and Segway tours. For more information and to make reservations, visit the website.

City Segway Tours Chicago, (877) 734-8687 or (312) 819-0186,

Take a guided tour of Chicago by riding a Segway. Tour types vary, as do the dates and times. Check the website for details. Prices for most tours available during the IA Summit start at $65-70 per person.

Meet for all tours at the City Segway Tours Chicago office at 910 S. Michigan Avenue, Suite 130, at the south end of Grant Park. The entrance is on 9th Street, steps away from the intersection of Michigan Avenue and 9th.

Untouchable Tours, (773) 881-1195,

Experience Chicago as it was during the 1920s and 1930s. Check out the old gangster hot spots and hit spots. Hear historically accurate accounts of the exploits of Capone, Moran, Dillinger, and the rest of the boys. This is a bus tour that cruises through the city in search of the old hoodlum haunts, brothels, gambling dens, and sites of gangland shootouts.

Tours last 1.75 to two hours, depending on traffic. Meet at 600 N Clark Street, near the intersection of Clark and Ohio Streets. You’ll stand on the west side of Clark Street, in front of a construction site where a new McDonald’s is being built.

Throughout March, tours are scheduled at 11 a.m. daily, with additional times on Friday, Saturday, and Sunday. Make reservations and pay online to ensure a spot. Tours cost $35 per person.

Wendella Sightseeing Company, (312) 337-1446,

Wendella offers a wide range of tours along the Chicago River and Lake Michigan, such as a lake cruise, architectural tours, bridge tours, sunset cruises, wine and cheese cruises, and cruises for special events like St. Patrick’s Day. Tours start March 16, and prices vary. Make reservations online.

Tours depart from two locations:

  • Main Dock, 400 N Michigan Avenue at the northwest corner of the Michigan Avenue Bridge (now known as the DuSable Bridge) at the base of the Wrigley Building (White Marble) on the Chicago River (1.3 miles from the Hilton Chicago)
  • Trump Dock, 401 N Wabash Avenue, at the west side of the Wrigley Building on the Chicago River (1.2 miles from the Hilton Chicago)

Urban Walks

The 606, (312) 742-4622,

The 606 runs along the Bloomingdale Trail for 2.7 miles from Ashland Avenue and N Ridgeway Avenue. There are 12 access points, about every quarter mile, along with a total of 17 ramps accessible to people with disabilities.

The 606 takes Chicago’s legacy of great parks to new heights. The 606 has the elevated Bloomingdale Trail as its centerpiece, connected to six neighborhood parks at ground level, a wheel-friendly event plaza, an observatory, art installations, educational programming, and other amenities. Set above city streets, it’s a new way to explore Chicago on trails for biking, running and strolling.

Some metered parking is available along the 606, but walking, cycling, and public transit are the recommended commuting modes to the trail.

Chicago Riverwalk,

This open pedestrian waterfront on the south bank of the Chicago River is a nice easy walk with beautiful views. Nicknamed the city’s “Second Lakefront”, the Riverwalk extends from Lake Shore Drive to Lake Street and has restaurants, park seating, boat rentals, and other activities.

Navy Pier, 600 E Grand Avenue, (312) 595-7437,

Navy Pier consists of more than 50 acres of parks, gardens, shops, restaurants, family attractions, and exhibitions on the shore of Lake Michigan. It’s rated among the top leisure destinations in the Midwest.

Hours: 10 a.m.-8 p.m. Monday-Thursday, 10 a.m.-10 p.m. Friday-Saturday, and 10 a.m.-7 p.m. Sunday

A view of Navy Pier at dusk from Chicago 360

There are also walking paths in the large green space at Grant Park and Millennium Park.

Millennium Park in Chicago

Chicago CityPASS Discount and Additional Tourist Information

If you’re visiting these attractions during your trip to Chicago, a CityPASS will help you save more than 50% of the total admission price to all venues:

  • Shedd Aquarium
  • Skydeck
  • The Field Museum
  • Museum of Science and Industry or 360 Chicago Observation Deck
  • Adler Planetarium or Art Institute of Chicago


Vouchers must be used within six months of purchase. Buy the CityPASS at

For more information and tourist ideas, visit these sites:

Sunset from Chicago 360

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