Guidebook for Chicago
Food Scene
If you walk approximately 4 blocks south on Oakley, you will hit a lovely, charming block that used to connect Little Italy to Taylor Street (where most think of Chicago’s Little Italy). There are magnificent restaurants, and you can have your fill of pasta and wine and stumble home :) You can look online at the menu but here’s my take on most of them. Ignotz is the least expensive and most casual, Ignotz has terrific pizza and a nice little bar to watch a game. The servers are family-level warm. Tell Roger I sent you!
50 locals recommend
Ignotz's
2421 S Oakley Ave If you walk approximately 4 blocks south on Oakley, you will hit a lovely, charming block that used to connect Little Italy to Taylor Street (where most think of Chicago’s Little Italy). There are magnificent restaurants, and you can have your fill of pasta and wine and stumble home :) You can look online at the menu but here’s my take on most of them. Ignotz is the least expensive and most casual, Ignotz has terrific pizza and a nice little bar to watch a game. The servers are family-level warm. Tell Roger I sent you!
Open since 1933, this place is Old School and insanely delicious. I recommend the linguine frutti di mare and the chicken cacciatore. There’s a bar up front with tables or the dining room in back.
6 locals recommend
Bruna's Ristorante
2424 S Oakley AveOpen since 1933, this place is Old School and insanely delicious. I recommend the linguine frutti di mare and the chicken cacciatore. There’s a bar up front with tables or the dining room in back.
This charming and recently redecorated place has a few outside tables for nice weather times. Wonderful food and a friendly chef. I had a divine risotto there.
6 locals recommend
La Fontanella Restaurant
2414 S Oakley AveThis charming and recently redecorated place has a few outside tables for nice weather times. Wonderful food and a friendly chef. I had a divine risotto there.
Fabulous, fun and tasty, this restaurant has great cocktails and terrific food, both Mexican and more traditional American fare like giant burgers. Also a few tables outside and a lot of neat art.
44 locals recommend
Pl-zen
1519 W 18th StFabulous, fun and tasty, this restaurant has great cocktails and terrific food, both Mexican and more traditional American fare like giant burgers. Also a few tables outside and a lot of neat art.
Don’t let the seafood-focused menu fool you - their meat and vegetarian items are also delicious. I love the Botana Mixta but then I love fish. They have a wide variety of cheladas and margaritas.
Mariscos Las Islitas
2446 S Western AveDon’t let the seafood-focused menu fool you - their meat and vegetarian items are also delicious. I love the Botana Mixta but then I love fish. They have a wide variety of cheladas and margaritas.
Tacos, glorious tacos. They are ridiculously good and cheap. I like the steak (bistec) but they’re all great. No booze here though. The escabeche (spicy pickled vegetables served with chips and salsa when you sit down) is sublime.
53 locals recommend
Taqueria Los Comales
1544 W 18th StTacos, glorious tacos. They are ridiculously good and cheap. I like the steak (bistec) but they’re all great. No booze here though. The escabeche (spicy pickled vegetables served with chips and salsa when you sit down) is sublime.
This is a little old fashioned greasy spoon diner/truck stop with all counter seating. I love their biscuits and gravy and ham off the bone. This place is popular now, so there’s often a wait on weekends.
Don's Grill
1837 S Western AveThis is a little old fashioned greasy spoon diner/truck stop with all counter seating. I love their biscuits and gravy and ham off the bone. This place is popular now, so there’s often a wait on weekends.
Delicious breakfast and lunch spot - fantastic food near a nice park (Arigo Park).
40 locals recommend
Stax Cafe
1401 W Taylor StDelicious breakfast and lunch spot - fantastic food near a nice park (Arigo Park).
This diner has good breakfasts, and it also has novelty sized enormous donuts the size of steering wheels.
11 locals recommend
Huck Finn Restaurant
3414 S Archer AveThis diner has good breakfasts, and it also has novelty sized enormous donuts the size of steering wheels.
I LOVE their steak tacos that come with rice, beans and coleslaw all inside. Also worth the trip for the gorgeous Mexican ceramics, even the sinks in the bathroom.
26 locals recommend
El Milagro Tortilla
1927 S Blue Island AveI LOVE their steak tacos that come with rice, beans and coleslaw all inside. Also worth the trip for the gorgeous Mexican ceramics, even the sinks in the bathroom.
Best sandwiches you’ll ever eat. Super cheap and the cafe displays local artists.
134 locals recommend
Cafe Jumping Bean
1439 W 18th St Best sandwiches you’ll ever eat. Super cheap and the cafe displays local artists.
PIZZA! Classic deep dish or try the meat and more meat (household favorite). Their salads are good too.
519 locals recommend
Giordano's
5311 S Blackstone AvePIZZA! Classic deep dish or try the meat and more meat (household favorite). Their salads are good too.
Classic Chicago deep dish with Mexican flair. Interesting cocktails too!
59 locals recommend
Gino's East
162 E Superior StClassic Chicago deep dish with Mexican flair. Interesting cocktails too!
Arts & Culture
This is the old site of the Chicago Public Library. It is SO beautiful. There is a giant domed Tiffany ceiling in Preston Bradley Hall (3rd floor), which has free concerts regularly - classical piano at noon on Wednesdays. The mosaic work in there is like something you would see in Italy.
203 locals recommend
Chicago Cultural Center
78 E Washington StThis is the old site of the Chicago Public Library. It is SO beautiful. There is a giant domed Tiffany ceiling in Preston Bradley Hall (3rd floor), which has free concerts regularly - classical piano at noon on Wednesdays. The mosaic work in there is like something you would see in Italy.
With spectacular woodwork and an old fashioned elevator with an operator, you will find violin makers, opera teachers, kundalini yogis and more in this building. It’s worth a trip and it’s near Millennium Park.
12 locals recommend
Fine Arts Building
410 S Michigan AveWith spectacular woodwork and an old fashioned elevator with an operator, you will find violin makers, opera teachers, kundalini yogis and more in this building. It’s worth a trip and it’s near Millennium Park.
Do NOT miss this attraction in walking distance. The exhibits, travelling and permanent, are extraordinary. And the gift shop is wonderful. The museum is a manageable size - not overwhelming like the Art Institute can be.
222 locals recommend
National Museum of Mexican Art
1852 W 19th StDo NOT miss this attraction in walking distance. The exhibits, travelling and permanent, are extraordinary. And the gift shop is wonderful. The museum is a manageable size - not overwhelming like the Art Institute can be.
A nice alternative to the Art Institute near Water Tower on the Gold Coast. Also located near the lake - good for walks.
532 locals recommend
Museum of Contemporary Art Chicago
220 E Chicago AveA nice alternative to the Art Institute near Water Tower on the Gold Coast. Also located near the lake - good for walks.
Shopping
Knee Deep Vintage
1219 W 18th StGreat vintage shop that's a short walk or a short bus ride.
Getting Around
Beautiful mosaic outside the station. I will likely have Ventra cards for you to use.
14 locals recommend
Western Pink Line Station
Beautiful mosaic outside the station. I will likely have Ventra cards for you to use.
Parks & Nature
31st Street Beach station
Great beach with a full bar/restaurant on the beach
Very beautiful park to go for a nice Sunday walk. Stick to daytime walks here though.
24 locals recommend
Douglas Park
Very beautiful park to go for a nice Sunday walk. Stick to daytime walks here though.
Lovely little secret park near Chinatown with trees and foliage specific to China. Also a water taxi spot and available for kayak rental.
39 locals recommend
Ping Tom Memorial Park
1700 S Wentworth AveLovely little secret park near Chinatown with trees and foliage specific to China. Also a water taxi spot and available for kayak rental.
Sightseeing
Millennium Park
201 E Randolph StWorth it - see the bean, the fountain, all of it!
Drinks & Nightlife
I cannot recommend this place highly enough. The beer is tremendous, the food is delicious and varied and there’s free live music. The only downside is that I don’t live there and that is closes at 9. You can get growlers of fresh beer to take back with you.
125 locals recommend
Lagunitas Brewing Company
2607 W 17th StI cannot recommend this place highly enough. The beer is tremendous, the food is delicious and varied and there’s free live music. The only downside is that I don’t live there and that is closes at 9. You can get growlers of fresh beer to take back with you.
Water Hole Lounge
1400 S Western AveLive music Wednesday and Friday. Walking distance. Fun times.