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catecath's Traveler List
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chicago tourist/1st time

Ask this member a question. catecath Local who recently relocated and miss the hell out of my hometown!
Sep 20, 2006
3.5 of 5 stars based on 2 votes
understanding of chicago neighborhoods (dining/activities)
  • Explore locations featured in this Traveler List: Chicago
  • Category: Perfect weekend
  • Traveler type: Culture, Shopping, Never been before, Repeat visitors
  • Appeals to: Couples/romantics, Singles, Students, Active/adventure
  • Seasons: Winter, Spring, Summer, Fall
  • Tags: weekend getaways, chicago neighborhoods
Check Rates ABS:HotelCheckRates-d111509?src=GoListDetail&fromServlet=GoListDetail&Action=QC_Button
Ave price: $228
Best location on Rush you can walk and see the Streeterville's neighborhoods--walk east and north a few blocks and you'll see beautiful houses. About a 30 min walk gets you to Old Town, north where you'll see more shops and a charming neighborhood. Walkable also to North Ave Beach and N part of Lincoln Park. That whole area is the highlight of Chicago shopping. MI ave is a few blocks away but it's more malls and designer high end shops.
2. Chicago Architecture Foundation
90 minute tours on the chicago river: history and view the beautiful city on the river. Drinks/snacks provided. Tickets from ticketmaster day prior or personally on the river at Wacker. They go fast during high season!
Yes it's a great walk from Oak go south, a good 45 min will get you into South Loop. Pass all the great shopping places (WaterTower/etc). Cross Tribune and Wrigley bldgs on Wacker is where Loop starts. Buckingham Fountains/Grant Park is east--After Art Institute, a few blocks further, go left and you'll run into them.
See and be seen. BEST of the places on Rush. Best cesar salad EVER! down the street from sutton place hotel
5. red head piano bar
Years and years ago I met the redhead. She had sold the place and was moving back south to New Orleans. She was SO cool. Real piano bar with pics of moviestars. Best time to go is weekdays if possible, lots of out of towners and business people. FUN!
On Rush St, this is also an establishment. Frank Sinatra's old bodyguard Jilly's opened it years ago. Smaller than Red Head, great martinis. See and be seen on the weekends! Steak restaurant as well and nighclub Syn downstairs.
TOTALLY OUT OF YOUR WAY but really worth the experience if you can do it. Al Capone and the mobsters used to hang at this '20s bar. They have different shows on different days but you'll get a mix of all kinds there. The booths are still from back in the day and it's a place all locals know. Take a cab to uptown. Not the greatest area uptown. There's a great mexican dive place next door FYI.
8. Oak Tree Restaurant (and also Bloomingdales)
Beautiful place in the Bloomindale's building top floor. Breakfast and Lunch. Duck with Mango Chutney sandwhich is to die for and the Chicken rice/noodle is homemade delicious. I always get it when I'm in town. Bloomies has more than just Bloomie's FYI, your top tier stores will be in there. For those that love top tier, visit Mark Shale.
ONLY GO to the one in west Loop, it's so much better. Southern cooking in Chicago. Esp. for brunch on sundays, you'll find a great mix of people there as well.
10. more casual dining while in S Loop
You'll find a lot of the waitstaff are students at CSO, Art Institute and/or other "artists" but go for the great drinks and food. "Diner" food but delicious. Specially the apple pie! Good place to stop to rest on MI ave after Art Institute or exploring S. Loop.
Blues, sweet blues and jazz. Great location d'town.
12. champagne bar/jazz club
2 locations, the better one is on Sheffield which you can cab to from d'town for about $12-15. I believe the new one is d'town, I have not been yet. Pops is just perfect for romance. StarBar is more casual for meeting up with friends. This is one of my fave places. Cover for live music on weekend is steep but menu/drinks delicious! Go for the ambiance.
You've heard of this right? Where all the stars started! Comedy is great. Walkable from hotel on a lovely warm summer night. In Old Town which is my old neighborhood and a beautiful one.
14. BEST LOBSTER RAVIOLI
cute cute charming neighborhood restaurant in Lakeview/Lincoln Pk. $10-15 cab ride. It'll get you into a non touristy part. Halsted is east. Great boutique shopping around as well esp if you head north toward Lincoln Pk. Not pricey.
15. local boutique Shopping
1. Southport. A few boutiques but they are wonderful. Lots of restaurants as well in this neighborhood. It's west and north, will be a lot to get to by taxi. Look at the el map for more info.
16. more local boutique shopping
2. Bucktown. Still crazy and great. West. $10-15 cab ride. The restaurants abound but I think they are less delicious and more trendy in this area. There are a couple high end like cafe absinthe that is great however. El takes you to the heart of bucktown. My favorite area for boutiques, esp. P45.
17. local shopping pt 3
3. Lincoln Park Halsted. It's a wide area. Start at Armitage and toward DePaul U there will be even more!!! Shop for women's and for home
18. shopping in general (honorable mentions :) )
handle with care is worth going to, they are wonderful. On North Ave in Old Town. The breadsmith next door is great. Material possessions on State d'town is a one of a kind, they go all over the world to find the most beautiful things shop. High end but delicious to look at.
19. Wacker
Wacker is a main street that curves. There is also a lower/upper Wacker. S. Loop is on S wacker (Sears Tower, Lyric Opera House, Chicago Merc Exchange). MI and Wacker is where the Tribune/Wrigley buldgs are. Also where you'll find tours for the city being sold.
20. River North/River West
Art galleries are located in River North. You'll find a lot of new condos/lofts in River West which also has a number of great swanky bars/restaurants.
21. Randolph street restaurants
Vivo and Blackbird are my favorites on this street well known as restaurant row. Located West Loop, close also to Little Italy and Greek Town, you'll also find a lot of lofts in this neighborhood. It's at the opposite end of the city from the hotel, $10-12 cab ride. Sushi Wabi for great sushi is there too. Those are my choices.
22. wrigleyville
obviously where wrigley field is :) North and east. It's also boys town, FYI. Gay Pride parade takes place each August which is quite a scream. You'll find good shopping esp. for ahem, the intimate kind and lingerie even. Go to a Cubs game if you even remotely like baseball. The field is small, every seat a good one but more interestingly, you'll never find anywhere else--people often pack the rooftops of neighborhood buildings to watch the games. They even charge for it! It's pretty cool to be in these surroundings, adding to the popularity of the ever losing cubbies :) Good architecture, food. Yoshi's is a Japanese place on Clark not too far. Take the El.
Explore locations featured in this Traveler List: Chicago