Guidebook for Chicago
Getting Around
Chicago's 'L' train system is the best way to get around the city's most popular spots. This stop, right around the corner from us, provides quick and frequent trips to The Loop--the main part of downtown. If you have Google Maps, switch it over the the Public Transit option and you'll have no trouble taking the train to your next stop.
Pro tip: there is a staircase on the far west side of the station that leads to an exit right on our street. This is particularly useful at night when our guests can enjoy the security of the train station all the way to our quiet little street.
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California & Lake station
Chicago's 'L' train system is the best way to get around the city's most popular spots. This stop, right around the corner from us, provides quick and frequent trips to The Loop--the main part of downtown. If you have Google Maps, switch it over the the Public Transit option and you'll have no trouble taking the train to your next stop.
Pro tip: there is a staircase on the far west side of the station that leads to an exit right on our street. This is particularly useful at night when our guests can enjoy the security of the train station all the way to our quiet little street.
I rent from here (and the 3 or 4 other convenient neighborhood locations) all the time. In my experience, Enterprise consistently has some of the best rates available. Plus you don't have to pay the airport surcharge.
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Enterprise Rent-A-Car
20 E Randolph StI rent from here (and the 3 or 4 other convenient neighborhood locations) all the time. In my experience, Enterprise consistently has some of the best rates available. Plus you don't have to pay the airport surcharge.
Friendly, honest, quick, convenient car repair. I hope you don't have to use this tip, but it's there if you need it.
JR Auto Rebuilders Mechanic Service
3240 W Carroll AveFriendly, honest, quick, convenient car repair. I hope you don't have to use this tip, but it's there if you need it.
Food Scene
Perfect for late nights! This 24-hour Mexican joint has great tacos, quesadillas, breakfast burritos and a lot more. It's about 5 minutes away by car and there is free parking right in front.
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Chavas Tacos El Original
2333 W Grand AvePerfect for late nights! This 24-hour Mexican joint has great tacos, quesadillas, breakfast burritos and a lot more. It's about 5 minutes away by car and there is free parking right in front.
Phone in an order or go to Grubhub to get delivery of a large amount of tasty pizza, fries and calzones. Their deep dish pizza is better than the better known Chicago pizzerias (exception: Lou Malnati's).
Bella Vita Pizzeria
3737 W Grand AvePhone in an order or go to Grubhub to get delivery of a large amount of tasty pizza, fries and calzones. Their deep dish pizza is better than the better known Chicago pizzerias (exception: Lou Malnati's).
I know this probably shouldn't make any sort of guidebook, but this place has the best shopping mall-style bourbon chicken that I have ever had. Order an extra side of rice, and it's easily 2 meals. Phone in a takeout order or put in your order before doing some grocery shopping at Pete's. If you don't have a car, I believe they deliver, as well.
King Wok
2323 W Madison StI know this probably shouldn't make any sort of guidebook, but this place has the best shopping mall-style bourbon chicken that I have ever had. Order an extra side of rice, and it's easily 2 meals. Phone in a takeout order or put in your order before doing some grocery shopping at Pete's. If you don't have a car, I believe they deliver, as well.
So far, this is our favorite Asian food in the city. Their selection goes beyond Sushi and Thai and incorporates other East Asian dishes. Recommended: The whole menu. Specifically: Pad Thai, Basil Fried Rice, any Sushi roll that has shrimp tempura.
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Butterfly Sushi Bar
1139 W Grand AveSo far, this is our favorite Asian food in the city. Their selection goes beyond Sushi and Thai and incorporates other East Asian dishes. Recommended: The whole menu. Specifically: Pad Thai, Basil Fried Rice, any Sushi roll that has shrimp tempura.
Take a break from the Magnificent Mile to grab some pork tacos
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Flaco's Tacos
1116 W Granville AveTake a break from the Magnificent Mile to grab some pork tacos
Great food, good prices, a bar and lots of TVs led Airbnb hosts to vote this restaurant and bar the "Top Spot to Catch a Game" on Chicago's West Side.
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The Ogden Chicago
1659 W Ogden AveGreat food, good prices, a bar and lots of TVs led Airbnb hosts to vote this restaurant and bar the "Top Spot to Catch a Game" on Chicago's West Side.
This is easily the best pizza that I have ever had. If you want to experience Chicago deep dish pizza, head to this location or one of the other Lou Malnati's restaurants scattered conveniently around town. They also have many carry-out only locations, so be sure you're not heading to one of those if you want to sit down and eat. I strongly suggest that you get two pizzas: one Lou (vegetarian) and one Classic (the opposite). They are both amazing. The menu helpfully, and pretty accurately, instructs you on how many people each pizza will feed. Further tips: you can order the pizza while you are waiting for your table so that it comes out soon after you are seated. Also, about those sizes I mentioned earlier ... round up and take some with you if it's convenient. It's just as good reheated in the oven.
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Lou Malnati's Pizzeria
1120 N State StThis is easily the best pizza that I have ever had. If you want to experience Chicago deep dish pizza, head to this location or one of the other Lou Malnati's restaurants scattered conveniently around town. They also have many carry-out only locations, so be sure you're not heading to one of those if you want to sit down and eat. I strongly suggest that you get two pizzas: one Lou (vegetarian) and one Classic (the opposite). They are both amazing. The menu helpfully, and pretty accurately, instructs you on how many people each pizza will feed. Further tips: you can order the pizza while you are waiting for your table so that it comes out soon after you are seated. Also, about those sizes I mentioned earlier ... round up and take some with you if it's convenient. It's just as good reheated in the oven.
Burrito Mex
6033 S Archer RdSimply some of the best Mexican food that I have ever had.
3 distinct Italian restaurants under one roof right in the middle of The Loop
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Italian Village Restaurant
71 W Monroe St3 distinct Italian restaurants under one roof right in the middle of The Loop
Drinks & Nightlife
The fanciest cocktails in the city come from this west side hideout that frequently is featured on lists of America's best bars. The drinks are expensive ($25+) but worth it for the unique taste and experience that each provides.
My recommendation: Get there early evening, especially on weekends, to avoid waiting in line. The drink prices don't seem so bad when you realize the complexity of each cocktail. Thus, you can sip your cocktail for the better part of an hour. If you bring good company, you'll enjoy yourself more than you would over the three microbrews that would set you back about the same amount time, money and sobriety. You might even decide to have another one.
If you don't want to travel to far for some food or more drinks, La Sirena Clandestina across the street is a friendly, low key, less expensive option.
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The Aviary
955 W Fulton MarketThe fanciest cocktails in the city come from this west side hideout that frequently is featured on lists of America's best bars. The drinks are expensive ($25+) but worth it for the unique taste and experience that each provides.
My recommendation: Get there early evening, especially on weekends, to avoid waiting in line. The drink prices don't seem so bad when you realize the complexity of each cocktail. Thus, you can sip your cocktail for the better part of an hour. If you bring good company, you'll enjoy yourself more than you would over the three microbrews that would set you back about the same amount time, money and sobriety. You might even decide to have another one.
If you don't want to travel to far for some food or more drinks, La Sirena Clandestina across the street is a friendly, low key, less expensive option.
Right across from The Aviary, this bar and restaurant also serves up some delicious cocktails.
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La Sirena Clandestina
954 W Fulton MarketRight across from The Aviary, this bar and restaurant also serves up some delicious cocktails.
Like other cities, Chicago has its own speakeasy inspired bar serving up meticulously crafted cocktails. House rules include "No cell phones" and "Don't bring anyone that you wouldn't bring to your mother's house for Sunday dinner." The cocktails here are pricey (~$15+), but they are worth it. Get there early evening or on weekdays to avoid the lines.
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The Violet Hour
1520 N Damen AveLike other cities, Chicago has its own speakeasy inspired bar serving up meticulously crafted cocktails. House rules include "No cell phones" and "Don't bring anyone that you wouldn't bring to your mother's house for Sunday dinner." The cocktails here are pricey (~$15+), but they are worth it. Get there early evening or on weekdays to avoid the lines.
This pub has a rotating selection of excellent beers and the bar tenders to guide you to your new favorite. Monk's is a short walk from the Clark & Lake train stop in the northwest corner of The Loop. Its hours cater to the folks working in nearby offices, so double check the hours before you go. (At the time of this writing, it is closed Sunday, only open until 5 on Saturday and closes at midnight during the week.)
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Monk's Pub
205 W Lake StThis pub has a rotating selection of excellent beers and the bar tenders to guide you to your new favorite. Monk's is a short walk from the Clark & Lake train stop in the northwest corner of The Loop. Its hours cater to the folks working in nearby offices, so double check the hours before you go. (At the time of this writing, it is closed Sunday, only open until 5 on Saturday and closes at midnight during the week.)
Division Street provides the closest area to bar hop in this convenient area in south Wicker Park. The Fifty/50 and Fatpour (try the Not Your Father's Root Beer) along Division and Rainbo Club a block south on Damen are personal favorites.
The Uber ride there probably won't even set you back $10. If you want to hop farther, hit this section up on your way to or back from the many bars around Damen and North Avenue.
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Divvy Station: Damen Ave & Division St
Division Street provides the closest area to bar hop in this convenient area in south Wicker Park. The Fifty/50 and Fatpour (try the Not Your Father's Root Beer) along Division and Rainbo Club a block south on Damen are personal favorites.
The Uber ride there probably won't even set you back $10. If you want to hop farther, hit this section up on your way to or back from the many bars around Damen and North Avenue.
Apparently pronounced "SHAM-blees" the traditional pronunciation is probably more fitting. While most bars close at 3 AM, this is the closest 4 AM bar ... just don't be surprised if the people there are exactly the people you'd expect to be out past the close of overything else.
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Shambles bar
2050 W Division StApparently pronounced "SHAM-blees" the traditional pronunciation is probably more fitting. While most bars close at 3 AM, this is the closest 4 AM bar ... just don't be surprised if the people there are exactly the people you'd expect to be out past the close of overything else.
Classy place in one of Chicago's skyscrapers. Outdoor seating in the summer. Good bartenders. Last time we were there, the Blackhawks were rumored to be stopping by later that night.
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Drumbar
201 E Delaware PlClassy place in one of Chicago's skyscrapers. Outdoor seating in the summer. Good bartenders. Last time we were there, the Blackhawks were rumored to be stopping by later that night.
Cool, small bar in Bucktown. Warning: cash only and there may be a line.
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Dannys
Cool, small bar in Bucktown. Warning: cash only and there may be a line.
Revolution's most popular beer, the Anti-Hero IPA, is widely distributed around Chicago and outlying neighborhoods. Chances are that you will see it at many restaurants, bars and stores during your trip. Their Brewing Tap Room gives you chance to sample a wide variety of their equally good but less distributed beers. Plus, they have free hourly tours that include a complimentary beer. Anti-Hero and some others are produced year round, but each season brings a unique line up of returning favorites and new creations. With over a dozen varieties on tap at any given time, there's sure to be something for everybody every time.
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Revolution Brewing - Brewery & Taproom
3340 N Kedzie AveRevolution's most popular beer, the Anti-Hero IPA, is widely distributed around Chicago and outlying neighborhoods. Chances are that you will see it at many restaurants, bars and stores during your trip. Their Brewing Tap Room gives you chance to sample a wide variety of their equally good but less distributed beers. Plus, they have free hourly tours that include a complimentary beer. Anti-Hero and some others are produced year round, but each season brings a unique line up of returning favorites and new creations. With over a dozen varieties on tap at any given time, there's sure to be something for everybody every time.
A great place to start or end a night out, particularly on St. Patrick's Day
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Emmit's Irish Pub
495 N Milwaukee AveA great place to start or end a night out, particularly on St. Patrick's Day
Richard's Bar
491 N Milwaukee AveSmoking inside is allowed. It smells like freedom.
Essentials
For our guests that are driving here, this is a great grocery store 5 minutes away. It has a wide selection including plenty of fresh produce, herbs, meat and seafood. (For our guests who aren't driving, let me know if you need anything, and I will pick it up.)
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Pete's Fresh Market
2333 W Madison StFor our guests that are driving here, this is a great grocery store 5 minutes away. It has a wide selection including plenty of fresh produce, herbs, meat and seafood. (For our guests who aren't driving, let me know if you need anything, and I will pick it up.)
Parks & Nature
Two stops away on the Green Line, the beautiful Garfield Park Conservatory is a great place to spend a relaxing afternoon. Airbnb hosts voted it the "Best Kept Secret" in Chicago's west side.
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Garfield Park Conservatory
300 N Central Park AveTwo stops away on the Green Line, the beautiful Garfield Park Conservatory is a great place to spend a relaxing afternoon. Airbnb hosts voted it the "Best Kept Secret" in Chicago's west side.
Humboldt Park is a scenic and gigantic park here on the West Side. Rolling hills, gardens and creeks encourage peaceful strolls. Paved trails allow for running or biking. As is the norm in Chicago, the park lends its name to the surrounding neighborhood. The large Puerto Rican population in this neighborhood make the park a fitting home to the National Museum of Puerto Rican Arts & Culture. Plus, this cultural influence makes the park the home of a pristine proturf soccer field and a handful of taco trucks.
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Humboldt Park
1400 N Humboldt DrHumboldt Park is a scenic and gigantic park here on the West Side. Rolling hills, gardens and creeks encourage peaceful strolls. Paved trails allow for running or biking. As is the norm in Chicago, the park lends its name to the surrounding neighborhood. The large Puerto Rican population in this neighborhood make the park a fitting home to the National Museum of Puerto Rican Arts & Culture. Plus, this cultural influence makes the park the home of a pristine proturf soccer field and a handful of taco trucks.
Chicago's best dog park is this wide open section of beach where your pooch can be off leash and run (or swim) around to its heart's content.
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Montrose Beach
Chicago's best dog park is this wide open section of beach where your pooch can be off leash and run (or swim) around to its heart's content.
Arts & Culture
Along with the PrivateBank Theatre and Cadillac Palace Theatre, the Oriental Theatre is home to many great Broadway shows. The tickets can be pricey, but the good shows are definitely worth it. As season ticket holders, we can provide info on the shows and may even have access to discounted tickets.
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James M. Nederlander Theatre
24 W Randolph StAlong with the PrivateBank Theatre and Cadillac Palace Theatre, the Oriental Theatre is home to many great Broadway shows. The tickets can be pricey, but the good shows are definitely worth it. As season ticket holders, we can provide info on the shows and may even have access to discounted tickets.
The iO Theatre is home to the Improvised Shakespeare Company on most weekends. The players perform in Shakespearean language an entirely improvised 2-act play based on a title suggested by the audience. The result is consistently hilarious.
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The iO Theater
1501 N Kingsbury StThe iO Theatre is home to the Improvised Shakespeare Company on most weekends. The players perform in Shakespearean language an entirely improvised 2-act play based on a title suggested by the audience. The result is consistently hilarious.
Chicago's best museum in my opinion is the Museum of Science and Industry. It's a little farther south than the other major Chicago museums, but it is easy enough to get to from the Green Line. Plan to spend all day there, though. There is a ton of interesting things to do whether you are 8 years old, 80 or in between.
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Museum of Science & Industry station
Chicago's best museum in my opinion is the Museum of Science and Industry. It's a little farther south than the other major Chicago museums, but it is easy enough to get to from the Green Line. Plan to spend all day there, though. There is a ton of interesting things to do whether you are 8 years old, 80 or in between.
The Second City
230 W North AveLegendary comedy venue
Sightseeing
A required stop for all Chicago tourists is to snap a picture of yourself in the giant, reflective Cloud Gate sculpture, known more commonly as "The Bean" for its shape. At the north end of Millennium Park, The Bean is right near the Art Museum, the park's amphitheater, many summer shows and events and some restaurants and cafes across the street. It is also possible to walk south across the park to the Field Museum, Soldier Field, the Planetarium and the Aquarium.
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Cloud Gate
201 E Randolph StA required stop for all Chicago tourists is to snap a picture of yourself in the giant, reflective Cloud Gate sculpture, known more commonly as "The Bean" for its shape. At the north end of Millennium Park, The Bean is right near the Art Museum, the park's amphitheater, many summer shows and events and some restaurants and cafes across the street. It is also possible to walk south across the park to the Field Museum, Soldier Field, the Planetarium and the Aquarium.
The Sears Tower Skydeck is totally touristy, but also very neat. Officially renamed the Willis Tower, this formerly tallest building in the world provides a 360 degree view of Chicago. The lines can get long, but a trip here can fit into almost any schedule. You can go at the beginning of your trip and get the lay of the land or at the end of your trip and see where you've been. You can go during the day and look out over Lake Michigan or at night and see the lights of the city. Just make sure to go when the skies are clear!
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Willis Tower Skydeck
The Sears Tower Skydeck is totally touristy, but also very neat. Officially renamed the Willis Tower, this formerly tallest building in the world provides a 360 degree view of Chicago. The lines can get long, but a trip here can fit into almost any schedule. You can go at the beginning of your trip and get the lay of the land or at the end of your trip and see where you've been. You can go during the day and look out over Lake Michigan or at night and see the lights of the city. Just make sure to go when the skies are clear!