Due to multiple requests, I’m posting information I compiled from various sources (i.e. friend’s suggestions, tour books, Yelp, etc.) for my first trip to Chicago in May 2009. I cannot guarantee that all information is still valid so please be sure to check the provided links.
PAM’S CHICAGO TRIP MAP – includes places mentioned below
PUBLIC TRANSIT
When taking public transportation in Chicago, NEVER pay with cash because you’ll pay $2.25 per trip, no transfers. I highly recommend the 1-day Fun Pass (at select locations, not many locals know about this) if you’re taking more than 2 bus/train rides in a 24-hour period or the refillable Transit Card (at any train station) if taking only 1 or 2 bus/train rides in a day. Plan ahead to save cash (I wish I had).
Unlimited-Ride Passes – activated on first use, passes allow unlimited rides for the specified time.
1-day: $5.75
3-day: $14
7-day: $23
Transit Cards – full fare with Chicago Card, Chicago Card Plus, and Transit Cards, allow value to be added
Fares
1st ride: $2.00 (bus); $2.25 (rail)
1st transfer: 25 cents
2nd transfer: FREE
Buy transit cards and passes from vending machines at various stations, select retail locations, CTA Headquarters, or online.
DINING
Fogo de Chao (Latin American, Brazilian, Steakhouses)
Neighborhoods: Near North Side, River North

Fogo de Chao Brazilian BBQ
Note: Go for lunch on a weekday, as it’s half price for the same menu.
Gibsons Steakhouse & Bar (Steakhouses, Italian)
Neighborhood: Near North Side
Note: Shares kitchen with Hugo’s Frog Bar, less wait at Hugo’s Frog Bar
Gino’s East (Pizza)
Neighborhoods: Near North Side, River East
Neighborhoods: Near North Side, River North
Giordano’s (Pizza)
Neighborhood: Near North Side
Neighborhood: The Loop

Giordano's special
Note: Thicker, crispier crust
Harold’s Chicken Shack (Fried Chicken)
Neighborhood: South Loop
Note: One of Obama’s favorites
Hot Doug’s (Hot Dogs)
Neighborhoods: Avondale
Note: Featured on Anthony Bourdain’s No Reservations; try duck fat fries and foie gras dog
Hugo’s Frog Bar (Seafood, Steakhouses)
Neighborhood: Near North Side

seafood dinner - stuffed lobster, crab cakes, salmon

raspberry sorbet, mud pie, chocolate mousse...and a quarter for size comparison
Note: Shares a kitchen with Gibsons Steakhouse
Joy Yee’s Noodles (Pan-Asian Cuisine)
Neighborhood: Chinatown

soft-shell crab and curry over rice
Note: HUGE bubble drinks, curry soft shell crab bowl
Kuma’s Corner (Pubs, Burgers)
Neighborhood: Avondale
Lawry’s The Prime Rib (Steakhouses)
Neighborhood: Near North Side
Lou Malnati’s (Pizza)
Neighborhoods: Near North Side, River North
Neighborhood: South Loop

sausage with roma tomatoes and spinach
Note: Thinner crust; better filling
Meli Cafe & Juice Bar (Breakfast & Brunch)
Neighborhoods: West Loop, Near West Side, Greektown

strawberry French toast
Note: Brunch and fresh juices
Portillo’s Hot Dogs (Hot dogs, American)
Neighborhoods: Near North Side, River North

beef n cheddar croissant
Note: Order the beef n cheddar croissant
RL Restaurant (Polo cafe; American)
Neighborhood: Near North Side
Note: Good for a brunch break from walking/shopping the Magnificent Mile
Volare (Italian)
Neighborhood: Near North Side
Note: MUST make reservations; otherwise they get very snippy at you and make you wait an hour. The food is really good, and it’s really romantic.
OTHER FOOD & DRINKS
Andy’s Jazz Club & Restaurant (Jazz & Blues)
Neighborhood: Near North Side
Artist’s Cafe
Neighborhood: The Loop
Note: Portions are really big, and they make their own French fries. It’s across the street and a few blocks down from the AIC.
Berry Chill (Frozen Yogurt)
Neighborhood: Near North Side
Note: Late hours at this location. Mon-Thu 8am-11pm, Fri-Sat 8am-2am, Sun 8am-11pm.
Neighborhood: The Loop

frozen yogurt and color-changing spoon
Billy Goat Tavern (Dive Bars, Burgers)
Neighborhoods: Near North Side, Magnificent Mile
Note: Famous dive that’s just one block from the Magnificent Mile and open after all the shops close. Tour buses and bachelorette parties stop here.
Caribou Coffee (Coffee & Tea)
Neighborhood: The Loop
Garrett Popcorn Shops (Specialty Food)
Neighborhood: The Loop
Note: Chicago mix is half caramel, half cheddar; caramel with macadamia nut is my favorite
Green Mill Cocktail Lounge (Jazz & Blues)
Neighborhood: Uptown
Kingston Mines Chicago Blues (Jazz & Blues)
Neighborhoods: Lincoln Park, DePaul
Mario’s Italian Lemonade (Italian Ice)
Neighborhood: University Village
Vosges Haut-Chocolat (Chocolatiers, Coffee & Tea)
Neighborhood: Near North Side (North Bridge Mall)
Neighborhoods: Lincoln Park, DePaul

gourmet chocolate bars
Note: Variety of unique gourmet chocolate blends; coffee and hot chocolate served.
SIGHTSEEING
Shoreline Sightseeing Architecture River Cruise (Tours)
Neighborhood: Near North Side

architectural boat tour
Note: MUST for first-timers and locals that haven’t taken the river tour
Adler Planetarium (Museums, Venues, Education)
Neighborhood: Near Southside
Note: Walk towards the planetarium at night for a sick view of the skyline.
Art Institute of Chicago (Museums)
Neighborhood: The Loop
Nore: Free after 5pm on Thu & Fri
The Modern Wing
Neighborhood: The Loop
Note: The biggest addition to the city’s cultural scene – opened May 16, 2009. Designed by star architect Renzo Piano, it will increase the museum’s size by one-third and provide a stunning showcase for the institute’s collection of modern art. A highlight of the design is the pedestrian bridge leading to Millennium Park, which will connect the museum to the park’s vibrant energy.
Buckingham Fountain in Grant Park (Parks)
Neighborhood: South Loop

Buckingham Fountain
Note: Fountain in opening credits of Married with Children
Frank Lloyd Wright Home and Studio (Museums, Landmarks)
City: Oak Park
Note: Entry into the museum is by guided tour only; guided tour length: 45-60 min. The Midwest’s greatest architect started out in the Chicago suburb of Oak Park, and his house, now a museum with guided tours, gives a first-hand look at his genius and his influence. The surrounding neighborhood, where Wright’s Prairie-style homes sit side-by-side with rambling Victorian villas, is an eye-opening lesson in architectural history.
Millennium Park (Parks; Behind the Art Institute)
Neighborhood: The Loop

Cloud Gate with Chicago skyline in reflection
Note: Look for the Frank Gehry-designed amphitheater (Jay Pritzker Pavilion), interactive Crown Fountain by Jaume Plensa, Anish Kapoor’s Cloud Gate sculpture on AT&T Plaza, and contemporary Lurie Garden. If it’s warm, people will sit on the boardwalk and stick their feet in the stream.
Signature Lounge (96th Floor of John Hancock Center; Landmarks)
Neighborhoods: Near North Side, Magnificent Mile, Streeterville

view from women's lounge
Note: Get a drink and skip admission; free view from women’s restroom
Willis Tower Skydeck Ledge (103rd Floor of Willis Tower; Landmarks)
Neighborhood: The Loop
Note: Opened July 2009. Enter Skydeck on Jackson Blvd
Wrigley Field (Stadiums)
Neighborhood: Lakeview
TIPS FROM FROMMER’S CHICAGO
Find out why the Loop is so named by hopping a Brown Line elevated train (or “the El,” for short). Watch the city unfold as the train crosses the Chicago River and screeches past downtown high-rises. Half the fun is peeping into the windows of offices and homes as you speed by (don’t feel guilty – we all do it).
It really is cooler – meteorologically and metaphorically – by the lake, and we Chicagoans treat the Lake Michigan waterfront as our personal playground. Miles of parkland hug the shoreline; walk to Monroe Harbor for picture-perfect views of the downtown or join active Lincoln Park singles for biking or jogging farther north. For an even better look at the city, get out on the water. At Navy Pier, you can board a vessel that’s just your speed, from a powerboat to a tall-masted schooner.
Exploring Millennium Park: This downtown park, carved out of the northwest corner of Grant Park, is Chicago’s newest great showcase (and it’s an easy walk from downtown hotels). While the Pritzker Music Pavilion, designed by Frank Gehry, is the highest-profile attraction, the park’s two main sculptures have quickly become local favorites. Cloud Gate, by British sculptor Anish Kapoor, looks like a giant silver kidney bean; watch your reflection bend and distort as you walk around and underneath. The Crown Fountain, designed by Spanish sculptor Jaume Plensa, is framed by two giant video screens that project faces of ordinary Chicagoans; it looks a little creepy at first, but watch the kids splashing in the shallow water and you’ll soon realize that this is public art at its best.