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re: Definitive Chicago Thread / Guide
Posted on 8/6/26 at 12:13 pm to hoopsgalore
Posted on 8/6/26 at 12:13 pm to hoopsgalore
Headed to Chicago for our honeymoon the first week of October (3rd through the 6th, before Chicago Marathon folks starting showing up for the next weekend).
Going to sit down this weekend and get booked where we're going to stay. Probably near the Art Institute and in that general area. Things that we are definitely doing, have reservations for already (if needed):
- The Girl and the Goat for dinner
- The Art Institute and the Russian tea house across the street (Russian Tea Time) with Millennium Park.
- Drinks at LondonHouse's rooftop bar (also weather pending, obviously)
Outside of that we're probably going to wing it. We've both been to Chicago before and done the Field Museum, Shedd's, Willis Tour/skydeck, Architecture Boat Tour. Neither of us care to hit Navy Pier at this point.
We do plan, if weather is decent to get out on one of the days to do some exploring and birding since it'll be fall migration period. Probably will hit up Montrose Point Bird Sanctuary (Lincoln Park) since it's a hot spot.
So suggestions are welcome (and definitely taking into consideration your lists but also any other suggestions folks have).
Going to sit down this weekend and get booked where we're going to stay. Probably near the Art Institute and in that general area. Things that we are definitely doing, have reservations for already (if needed):
- The Girl and the Goat for dinner
- The Art Institute and the Russian tea house across the street (Russian Tea Time) with Millennium Park.
- Drinks at LondonHouse's rooftop bar (also weather pending, obviously)
Outside of that we're probably going to wing it. We've both been to Chicago before and done the Field Museum, Shedd's, Willis Tour/skydeck, Architecture Boat Tour. Neither of us care to hit Navy Pier at this point.
We do plan, if weather is decent to get out on one of the days to do some exploring and birding since it'll be fall migration period. Probably will hit up Montrose Point Bird Sanctuary (Lincoln Park) since it's a hot spot.
So suggestions are welcome (and definitely taking into consideration your lists but also any other suggestions folks have).
Posted on 8/8/26 at 6:41 am to BluegrassBelle
quote:
- The Girl and the Goat for dinner
West Loop classic and pioneer. No longer the standard, per se, but we can always count on consistently good food and even better service.
I don't think the WL cocktail bar scene is great, at least compared to Logan Square and West Town, but head to Booze Box or Bisous for a drink. Honorable mention for The Hoxton's lobby bar - Lazy Bird is a cocktail bar downstairs but can get crowded.
quote:
- Drinks at LondonHouse's rooftop bar (also weather pending, obviously)
Incredible views down the river. If I can toss out another option, consider The Up Room inside The Robey. In my opinion, best skyline view of the city.
quote:
Probably will hit up Montrose Point Bird Sanctuary (Lincoln Park) since it's a hot spot.
Not Lincoln Park, just as an FYI, but this is a great idea. Beautiful area.
If you have any other cuisine preferences, happy to provide more pointed recommendations. Fine dining is, of course, great but Chicago has the second largest Mexican-American population in the country, for example, so no shortage of hole-in-the-wall spots.
This post was edited on 8/8/26 at 9:59 am
Posted on 8/8/26 at 10:41 am to hoopsgalore
quote:
If you have any other cuisine preferences, happy to provide more pointed recommendations. Fine dining is, of course, great but Chicago has the second largest Mexican-American population in the country, for example, so no shortage of hole-in-the-wall spots.
We will eat a Chicago dog (drug through the garden) from a cart as well as sit down spots. We’re pretty much game for any spot. And we eat a ton of ethnic food here in Louisville with Thai, Indian, Vietnamese, Caribbean, Nigerian, Mexican, etc. so we’re also game for that if you have some good spots.
Our favorite local Mexican spot here is actually Mayan-Yucatán cuisine (recommend if you’re ever here in Louisville) at Mayan Cafe
Posted on 8/8/26 at 7:31 pm to hoopsgalore
Drawing closer to our trip- 2 weeks to be exact. Trying to figure a three day itinerary is tough, so much to do. I’m starting to feel like Clark Griswold.
Since we’re staying in Albany Park, we’ll probably stay on the Northside the first afternoon/evening. Lincoln Square has my curiosity. Maybe get down to Lincoln Park and check out Kingston Mines.
I’m taking your recs on Chinatown, Pilsen and Bucktown. I’m getting the C3 pass and doing the Skydeck, Field and the Architecture boat tour. Honestly, the train excites me the most lol. I’m a huge railfan and love good public transportation. The only transit I’m used to is LexTran in Lexington and TARC in Louisville, both bus services. Getting around Chicago without a car just sounds cool to me.
Thanks for all you do, you’re a great resource/guide to Chicago.
Since we’re staying in Albany Park, we’ll probably stay on the Northside the first afternoon/evening. Lincoln Square has my curiosity. Maybe get down to Lincoln Park and check out Kingston Mines.
I’m taking your recs on Chinatown, Pilsen and Bucktown. I’m getting the C3 pass and doing the Skydeck, Field and the Architecture boat tour. Honestly, the train excites me the most lol. I’m a huge railfan and love good public transportation. The only transit I’m used to is LexTran in Lexington and TARC in Louisville, both bus services. Getting around Chicago without a car just sounds cool to me.
Thanks for all you do, you’re a great resource/guide to Chicago.
This post was edited on 8/8/26 at 7:33 pm
Posted on 8/9/26 at 12:04 am to BluegrassBelle
quote:
We will eat a Chicago dog (drug through the garden) from a cart as well as sit down spots. We’re pretty much game for any spot. And we eat a ton of ethnic food here in Louisville with Thai, Indian, Vietnamese, Caribbean, Nigerian, Mexican, etc. so we’re also game for that if you have some good spots.
Carts and trucks are around but heavily regulated. That said, my two favorite Chicago dogs are at Bangers & Lace in Wicker, which is a great beer bar, and Austin's Street Wieniers. Latter is this dude Austin that sets up shop in Avondale on Saturdays.
Have a Jibarito while you're here - Jibaritos y Mas and Smash Jibarito are fantastic.
In Chinatown, Nine Bar (No. 76 on 50 Best in North America) is a worthwhile cocktail bar. For food, go with MCCB, QXY, Triple Crown, or Phoenix. These are the four most popular restaurants in the area, so choosing one will be good for a first time visitor.
Chicago has the second-largest Mexican American population in the country, which I've mentioned in the past. No shortage of great Mexican restaurants, but it's different than San Diego, which people love to compare. SoCal is almost entirely Baja style, whereas Chicago is more represented by central and southern Mexican states. In Pilsen, I'll steer you to some popular spots to make it easy: Don Pedro, QuesaBirria Jalisco, La Luna, El Milagro, and Rubi's.
There is a cluster of African restaurants in Uptown, but Demera reigns supreme - One of the best casual eats in the city. This is also near a smaller Chinese and Vietnamese driven part of Argyle. Sun Wah BBQ is where you want to go.
This post was edited on 8/10/26 at 5:07 pm
Posted on 8/9/26 at 12:08 am to BluegrassCardinal
quote:
Honestly, the train excites me the most lol. I’m a huge railfan and love good public transportation.
Very excited for you, man, especially being on the Brown Line. Elevated the entire run, so you'll get some very fun looks at neighborhoods from above.
Posted on 8/9/26 at 12:09 pm to BluegrassCardinal
quote:
The only transit I’m used to is LexTran in Lexington and TARC in Louisville, both bus services. Getting around Chicago without a car just sounds cool to me.
You’re going to get spoiled with public transport in Chicago. And it’ll make you irrationally angry when you come back as to why we can’t have something serviceable.
In all seriousness, last time I visited I took the train or walked a lot of places. Took a cab to the CIBC to see Hamilton. Pretty much parked the car at the hotel the whole time.
Posted on 8/10/26 at 1:39 pm to hoopsgalore
quote:
Carts and trucks are around but heavily regulated. That said, my two favorite Chicago dogs are at Bangers & Lace in Wicker, which is a great beer bar, and Austin's Street Wieniers. Latter is this dude Austin that sets up shop in Avondale on Saturdays.
Have a Jibarito while you're here - Jibaritos y Mas and Smash Jibarito are fantastic.
In Chinatown, Nine Bar (No. 76 on 50 Best in North America) is a worthwhile cocktail bar. For food, go with MCCB, QXY, Triple Crown, or Phoenix. These are the four most popular restaurants in the area, so choosing one will be good for a first time visitor.
Chicago has the second-largest Mexican American population in the country, which I've mentioned in the past. No shortage of great Mexican restaurants, but it's different than San Diego. Region like SoCal is almost entirely Baja style, whereas Chicago is more represented by central and southern Mexican states. In Pilsen, I'll steer you to some popular spots to make it easy: Don Pedro, QuesaBirria Jalisco, La Luna, El Milagro, and Rubi's.
There is a cluster of African restaurants in Uptown, but Demera reigns supreme - One of the best casual eats in the city. This is also near a smaller Chinese and Vietnamese driven part of Argyle. Sun Wah BBQ is where you want to go.
All sounds delicious. So some further questions (if you don't mind):
1. We're staying at the Chicago Athletic Association (nerding out a bit over the architecture/design). Outside of what's on the premise (we'll probably catch dinner at The Ives) what are your eatery suggestions for the general area? Figured if we have any weather issues, we could keep it close to the hotel.
2. Any food suggestions for around the Montrose Bird Sanctuary area?
3. I'd like to surprise the fiance with a stop at a Jazz bar. Suggestions?
Posted on 8/10/26 at 2:01 pm to BluegrassBelle
quote:
1. We're staying at the Chicago Athletic Association (nerding out a bit over the architecture/design). Outside of what's on the premise (we'll probably catch dinner at The Ives) what are your eatery suggestions for the general area? Figured if we have any weather issues, we could keep it close to the hotel.
To be candid, as you may have noticed from my OP, the Loop is very much geared toward the weekday work crowd. Compared to other Chicago neighborhoods, the dining scene is fairly average. That said, there are still some excellent options nearby. Right next to CAA, I'd recommend Acanto and The Gage. Miller's Pub is another great choice and a Chicago institution, and Bistro Monadnock is also worth checking out.
If you're visiting during the week, be sure to stop by Sterling Hall. It's a food hall with quite a few good vendors. Just keep in mind that it's closed on weekends.
quote:
2. Any food suggestions for around the Montrose Bird Sanctuary area?
Apologies, I can't remember exactly when you'll be in town, but Carino was the first place that came to mind for something pricier. They've earned a Michelin star and currently offer one of the best new tasting menus in the city. If you're looking for something a bit more casual and fun, they also do a late-night taco omakase that's a little more affordable.
Regarding your earlier questions about ethnic food, Uptown/Buena Park are the immediate neighborhoods near Montrose Beach / Bird Sanctuary and this is where you'll find Demera, Sun Wah, etc. Montrose is a big space, though, so it'll be a longer walk or quick rideshare to most restaurants.
If you want to grab a quick drink after the bird sanctuary, check out The Dock at Montrose Beach. Great beach bar.
*Saw you'll be here in October, so rules this out*
And if you're interested in cocktails, Larry's at The Lawrence House is definitely worth a visit. I mentioned it in my OP.
quote:
3. I'd like to surprise the fiance with a stop at a Jazz bar. Suggestions?
The Green Mill and Kingston Mines are very famous jazz clubs on the north side. Coincidentally, the former is right there with you in Uptown.
This post was edited on 8/10/26 at 5:09 pm
Posted on 8/10/26 at 2:13 pm to hoopsgalore
quote:
To be candid, as you may have noticed from my OP, the Loop is very much geared toward the weekday work crowd. Compared to other Chicago neighborhoods, the dining scene is fairly average. That said, there are still some excellent options nearby. Right next to CAA, I'd recommend Acanto and The Gage. Miller's Pub is another great choice and a Chicago institution, and Bistro Monadnock is also worth checking out. If you're visiting during the week, be sure to stop by Sterling Hall. It's a food hall with quite a few good vendors. Just keep in mind that it's closed on weekends.
Yeah we’re going up on Saturday but coming back on Wednesday so we’ll have Monday and Tuesday there.
I had Miller’s Pub coming back from the CIBC on my last stay. Had a great fish sandwich there.
ETA: We’ll definitely check out the food hall. That’s definitely up our alley.
We're in town first week of October
This post was edited on 8/10/26 at 2:32 pm
Posted on 8/12/26 at 9:47 pm to hoopsgalore
Just chiming in that we did take the kids down to Chinatown. Really couldn’t recommend hoping on the river taxi more. My kids loved every minute of the boat ride there and back.
Other ferry boats gave great waves back to my kids. Private yacht owners are stone cold bitches won’t can’t be bothered to acknowledge us plebes.
Golden Bull was a great restaurant, but this excursion was all about the boat ride.
Other ferry boats gave great waves back to my kids. Private yacht owners are stone cold bitches won’t can’t be bothered to acknowledge us plebes.
Golden Bull was a great restaurant, but this excursion was all about the boat ride.
Posted on 8/13/26 at 10:57 am to hoopsgalore
quote:
Apologies, I can't remember exactly when you'll be in town, but Carino was the first place that came to mind for something pricier. They've earned a Michelin star and currently offer one of the best new tasting menus in the city. If you're looking for something a bit more casual and fun, they also do a late-night taco omakase that's a little more affordable.
Regarding your earlier questions about ethnic food, Uptown/Buena Park are the immediate neighborhoods near Montrose Beach / Bird Sanctuary and this is where you'll find Demera, Sun Wah, etc. Montrose is a big space, though, so it'll be a longer walk or quick rideshare to most restaurants.
If you want to grab a quick drink after the bird sanctuary, check out The Dock at Montrose Beach. Great beach bar.
*Saw you'll be here in October, so rules this out*
And if you're interested in cocktails, Larry's at The Lawrence House is definitely worth a visit. I mentioned it in my OP.
Sun Wah is one of my favorites places to bring out of town guests. I'd add Kie-Gol-Lanee to the list of post Montrose options. Fantastic Oaxacan restaurant.
You might also check out Lemon and Dorian's for jazz
This post was edited on 8/13/26 at 11:24 am
Posted on 8/13/26 at 12:51 pm to keakdasneak
quote:
'd add Kie-Gol-Lanee to the list of post Montrose options. Fantastic Oaxacan restaurant.
Good call on Kie-Gol-Lanee. Sort of forget OG because I go to their Logan location.
quote:
You might also check out Lemon and Dorian's for jazz
I was thinking about Dorian's, but TikTok has made it quite an annoying place to be
Couple that with a $10 cover, I'd probably just pay the extra $5-10 and go to one of the famous clubs as a weekend visitor. Totally agree with Lemon, though - A lot of space and good cocktails. Also, walking distance to Friends of Friends, Bar Bambi, etc.
Posted on 8/13/26 at 1:35 pm to hoopsgalore
quote:
I was thinking about Dorian's, but TikTok has made it quite an annoying place to be
Good to know!
"Come with me to a hidden gem I discovered..."
Posted on 8/13/26 at 2:41 pm to keakdasneak
Exactly!Posted on 8/17/26 at 9:44 am to hoopsgalore
SIAP, but I will be in Chicago next weekend for some cubs games and saw the Sunday night game got moved to 6:30. Is the train safe to take back to our hotel downtown after the game?
Posted on 8/17/26 at 9:55 am to Rooster2023
quote:
Is the train safe to take back to our hotel downtown after the game?
Yes, you'll be fine (and it'll be crowded). Enjoy
Posted on 8/24/26 at 12:03 pm to hoopsgalore
Hoopsgalore, thanks for the thread! We are heading home and had a great time.
Some highlights:
Friday we were at MSI and saw the Anne Frank exhibit. Very powerful. Then some deep dish pizza at Lou Malnati’s in Lincoln Park.
Saturday we visited the Ledge on Sears tower. Wicker Park and Chinatown.
Yesterday, the architecture boat tour, Pilsen, and then walked up Michigan Ave. Today we had breakfast at Bryn Mawr Breakfast club in Ravenswood, then we visited the firehouse where they film some of Chicago Fire at. The guys were fantastic and showed us around the firehouse.
Incredible city, absolutely loved it. Pilsen was my favorite neighborhood. Very authentic, had incredible quesabirria tacos, and checked out a really cool art museum- National Museum of Mexican Art.
We rode the trains everywhere- CTA and the ME to Jackson Park. 15 bucks for a three day pass on the CTA was a bargain, and a fun experience.
I thought about you when we stopped at Lottie’s in Bucktown. You mentioned it was a Wisconsin bar. One of the servers mentioned its’s also a Kansas bar. We saw some ads for watch parties for Wisconsin and Kansas’s kickoff games.
Great city, already thinking of a return trip soon.
Some highlights:
Friday we were at MSI and saw the Anne Frank exhibit. Very powerful. Then some deep dish pizza at Lou Malnati’s in Lincoln Park.
Saturday we visited the Ledge on Sears tower. Wicker Park and Chinatown.
Yesterday, the architecture boat tour, Pilsen, and then walked up Michigan Ave. Today we had breakfast at Bryn Mawr Breakfast club in Ravenswood, then we visited the firehouse where they film some of Chicago Fire at. The guys were fantastic and showed us around the firehouse.
Incredible city, absolutely loved it. Pilsen was my favorite neighborhood. Very authentic, had incredible quesabirria tacos, and checked out a really cool art museum- National Museum of Mexican Art.
We rode the trains everywhere- CTA and the ME to Jackson Park. 15 bucks for a three day pass on the CTA was a bargain, and a fun experience.
I thought about you when we stopped at Lottie’s in Bucktown. You mentioned it was a Wisconsin bar. One of the servers mentioned its’s also a Kansas bar. We saw some ads for watch parties for Wisconsin and Kansas’s kickoff games.
Great city, already thinking of a return trip soon.
Posted on 8/24/26 at 12:15 pm to BluegrassCardinal
Glad you had a great time. and thrilled you enjoyed Pilsen. Truly, it is such a cool neighborhood. Yup, Lottie's (I'm assuming you went there with the Chicago Fire connection) doubles as a Wisconsin / Kansas bar but it's the closest Wisconsin bar to anyone living in Wicker/Bucktown/Logan. Otherwise, Wills and Ranalli's are good options in Lakeview and Lincoln Park!
In an otherwise rainy/stormy summer, weather was gorgeous this weekend - We took full advantage. Went to Gilda's and Bar Bambi on Friday (add Gilda to your list). We did a 4+ mile walk down Lakeshore Trail on Saturday morning, followed by a tavern-style at Zarella. Went out with some friends for the afternoon around Wicker and River West. Saturday night, went to dinner with another couple and grabbed cocktails at Union in Logan Square.
Paid for it yesterday
In an otherwise rainy/stormy summer, weather was gorgeous this weekend - We took full advantage. Went to Gilda's and Bar Bambi on Friday (add Gilda to your list). We did a 4+ mile walk down Lakeshore Trail on Saturday morning, followed by a tavern-style at Zarella. Went out with some friends for the afternoon around Wicker and River West. Saturday night, went to dinner with another couple and grabbed cocktails at Union in Logan Square.
Paid for it yesterday
This post was edited on 8/24/26 at 10:49 pm
Posted on 8/24/26 at 8:15 pm to hoopsgalore
quote:
That said, my two favorite Chicago dogs are at Bangers & Lace in Wicker, which is a great beer bar,
Bangers and Lace was always a must stop for me but it’s sadly a shell of itself now. The menu never recovered from COVID and it’s just a joke now. I’m sure it’s still a great place to drink but come on, they don’t even try with food these days.
This post was edited on 8/24/26 at 8:28 pm
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