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Mar 8, 2013 02:41 PM

First Chicago Trip!

Hi everyone,

My girlfriend and I are going to be heading to Chicago next weekend for a five day, four night trip (our first trip together too!). I'm a pretty big food guy, and have tried to eat out as much as possible in NYC (where I used to live) and Boston (where I live now), and am trying to do the same while in Chicago. My girlfriend, on the other hand, doesn't love fine dining like I do, so we agreed that we would do one very fancy place, and keep the rest casual. I got us tickets for Alinea on Sunday night. Here is our planned itinerary. Feel free to comment on the food or activity choices below!


Arrive at noon; Park Hyatt Chicago
St. Patrick’s Day Parade
Xoco for dinner
Blues/jazz (thinking B.L.U.E.S, but suggestions welcome!)

Brunch? Any ideas? Want to keep it light.
Magnificent Mile

Switch hotel to Waldorf Astoria
Little Goat Diner/Au Cheval for breakfast
Loop/Millennium Park
Lunch? Any ideas?
Museum of Contemporary Photography
Dinner? Any ideas?
NBA game - United Center

Bongo Room for breakfast?
Frank Lloyd Wright (Oak Park)
What about Tuesday night dinner and activities?

Flight at 11am

Obviously I have a lot of "gaps" for meals, and that's where I could use help. Looking for casual, but nice places for both lunch and dinner. My girlfriend is a vegetarian, but I would consider myself more of a carnivore than anything else, which makes our relationship a little tough when it comes to food.

Also thinking about doing a nicer (but not Alinea nice) restaurant on Tuesday night; any ideas of a upscale, romantic place?

Thanks so much for any advice!!

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  1. >> Xoco for dinner

    Not what I would recommend for dinner. One of Chicago's strengths is our contemporary Mexican cuisine. However, that's not what Xoco serves; theirs is more along the lines of "Mexican street food", including tortas (sandwiches), caldos (soups), etc. I might include it for breakfast or maybe for lunch. But for dinner, I'd instead go to one of our contemporary Mexican places - either its sister restaurant, Frontera Grill (if you can snag a reservation, or can arrive before they open the doors, or don't mind a long wait to be seated), or one of the other good places for such fare: Mexique, Mundial Cocina Mestiza, Mixteco Grill, or Salpicon.

    >> Sunday
    >> Brunch? Any ideas? Want to keep it light.

    Near your hotel, Cafe des Architectes serves a very nice a la carte brunch, and they give you a complimentary basket of French breads and pastries. They accept reservations, too (you may or may not need them).

    Near the Aquarium, you could go to Bongo Room, one of our breakfast-focused restaurants; however, they don't take reservations, and waits on a Sunday could be lengthy. Be careful ordering though! They specialize in creative pancake dishes, like pretzel pancakes with white chocolate caramel sauce. Their standard portion consists of three GIGANTIC pancakes and will stuff you for sure. However, you can order one-third or two-thirds portion sizes at reduced prices, and this is a good way to go if you want to keep it light.

    >> Loop/Millennium Park
    >> Lunch? Any ideas?

    Pizano's on Madison for deep-dish. The Gage for gastropub fare. Park Grill if you want light American fare, such as a good burger. Terzo Piano for Italian; it's in the modern wing of the Art Institute, but you don't have to pay admission to the museum to eat there. Or tesori, another very good Italian place nearby.

    >> Dinner? Any ideas?
    >> NBA game - United Center

    You're going to want to eat early; games usually start at 7. I'd make a reservation at Sable no later than 5:00, or maybe try walking in at Purple Pig by 4:30 (if the wait then is already lengthy, Sable is a short walk from there).

    >> Tuesday
    >> Bongo Room for breakfast?


    >> What about Tuesday night dinner and activities?

    You have a lot of options for dinner. Just to give you some ideas, here are a couple of paragraphs excerpted from a post I wrote earlier today in another topic ( ):

    There are several restaurants which offer terrific food along with a fine-dining experience, but without that high a price tag (and where the dress code isn't quite as formal - e.g. jackets not required for men). Three of these in the $110-140/pp range are Acadia, North Pond, and Naha (although you can spend more than that if you go for the tasting menu and/or high-end wine). Acadia is relatively new (one year old); I loved it when I ordered a la carte, not as much when I had the tasting menu. North Pond is always wonderful, not only for the food, but also for the exquisite setting in the middle of the park, facing the pond with the city skyline looming over the far shore. Naha is outstanding also. Both North Pond and Naha are headed by chefs who won the James Beard Award for Best Chef - Great Lakes.
    Also in the "not so expensive" price category, some of our very best restaurants, with some of our most creative chefs, offer a small plates format on the menu. These include Sable (contemporary American small plates, craft cocktails), GT Fish & Oyster (seafood small plates, craft cocktails), and Mercat a la Planxa (tapas), all of which accept reservations, including on Opentable. The Purple Pig, with Mediterranean-ish small plates, is also one of our best; however, it doesn't accept reservations, and waits to be seated are horrendous (120+ minutes between 5 and 10 pm); I recommend trying it mid-afternoon or very late at night.

    Note that we're not supposed to stray from food/beverage in our conversations. If you're looking for ideas regarding activities, you may want to check out the city's tourism website at

    >> Wednesday
    >> Flight at 11am

    If you're willing to get up early, you might be able to squeeze in a meal at one of our great breakfast-focused restaurants. For example, Jam opens at 7 a.m. and it's right on the way to O'Hare, just a couple of blocks from the Logan Square station on the CTA Blue Line. Jam is owned/run by Jeffrey Mauro, who has worked in fine-dining places like Charlie Trotter's, and you can imagine what kind of creative fare he serves, while still keeping it casual and moderately-priced as a breakfast place.

    >> Also thinking about doing a nicer (but not Alinea nice) restaurant on Tuesday night; any ideas of a upscale, romantic place?

    Going back to the first of the two paragraphs I quoted above, North Pond is perfect for this - great food combined with an amazingly romantic setting in the middle of the park. When making your reservation, ask for seating in the front room with the view of the pond.


    4 Replies
    1. re: nsxtasy

      Helped immensely - thank you! Going to Sable Tuesday night, and still working out the other details. Wish I could go to the Purple Pig, but it doesn't seen very vegetarian-friendly, so I'll avoid the fight with my girlfriend over it.

      1. re: extremepc

        Take another look at the Purple Pig menu. Their vegetable antipasti and salads are excellent, they have a cheese list too. Unless she's picky, it should be ok.

        1. re: extremepc

          My gf and i didn't have much trouble ordering veggie items from Purple Pig, and honestly they may have been the best (though everything was really great). If you can swing it (ie, deal with the crowds/no reservations), def. do purple Pig.

          We recently ate at Sable and although it was ok, we were fairly disappointed (expected it to be pretty good). The cheese curds were not very good, the kale was greasy, and i feel like there was another dish I just can't even remember that was disappointing. The lamb sliders were good though and the carmelized onion flatbread (really a small pizza) was very good. And we actually felt a little restricted by their "healthy" options, which my gf always likes to have a good balance of.

          1. re: mdpilam

            The best dishes at Sable include their duck sausage with pistachio, sweet corn creme brulee, and whatever panna cotta they have for dessert. I had a reuben strudel dish there that I loved, but it wasn't on the menu during my most recent visit.

      2. For Tuesday while in Oak Park, head over to Elmwood Park and Johnnie's on North Ave. for the best Italian Beef in Chicagoland. It's about a five minute trip by car and remember to order it "juicy".

        2 Replies
        1. re: hoppy2468

          If you are taking public transit to Oak Park, instead of Johnies, you might want to try Katy's Dumplings, which just opened in OP on Lake St, near Harlem -- walkable from the FLW home and very close to the Harlem stop of the green line. It's the latest branch of a highly acclaimed family-owned business in the western suburbs of Chicago. The Oak Park resto just opened this week but, if it is like its sister restaurants (the original is in Westmont and a second is in Naperville), it should be great.

          1. re: masha

            Another good option in Oak Park is Eyrie. It's staffed by students in the culinary/hospitality program at Robert Morris College. Open for lunch only according to their website, although when I had an excellent lunch there some months ago they had a sign up about doing dinner once a month.

        2. Thank you to all for their great suggestions, especially nsxtasy - thank you for taking the time to type all of that up!!

          Does anyone have any spots similar to Noth Pond (romantic, etc.) by without QUITE the same $$; I'm thinking $100-$125 all-in (w/o wine).

          3 Replies
          1. re: extremepc

            >> Does anyone have any spots similar to Noth Pond (romantic, etc.) by without QUITE the same $$; I'm thinking $100-$125 all-in (w/o wine).

            Sure! Here are a few suggestions for nice places with great food along with a lower price tag.

            Sable, which I mentioned above, is an amazing bargain. Most of their items are available in half portions, and you can order three of those half portions per person for around $30 and you'll be well satisfied. It's somewhat noisy and trendy, with an open kitchen on one side of the main dining room. It's walkable from the Waldorf.

            La Sardine is an excellent French bistro in the West Loop. On Tuesdays they have a special, any three courses for $27.50 (although on other days of the week, it's not all that much more than that anyway). The vibe is busy bistro. You'll want to make reservations, especially on Tuesdays when they fill up due to that special. They accept reservations on their own website (but not Opentable), as well as over the phone.

            Another place I enjoy a lot is Deleece, on Southport in Lakeview. They serve excellent contemporary American cuisine, in a cozy neighborhood bistro setting. Prices are moderate, with most entrees around $20. It's about 4 miles from the hotel; by public transit, you could take the CTA Red Line to Addison, or the Brown Line to Southport, or the #22 Clark St bus to Grace Street (the bus takes the longest but involves the shortest walk at that end).

            One final suggestion is a bit off-beat and in an inconvenient location, but it's excellent and romantic. Han 202 is in Bridgeport, four miles south of the Loop, and getting there by public transit is indirect. It's BYOB, and they serve a five-course prix fixe menu for $25, with $5 supplements on a few items. Some of the menu is Chinese fare, and some of it is French.

            La Sardine and Han 202 always have dessert souffles on the menu, and they're excellent.

            Incidentally, if you would like to experience North Pond without the high price tag, they're also open for Sunday brunch, $33 for 3 courses prix fixe.

            1. re: nsxtasy

              Here's one more suggestion of a great place with a low price tag, which I just remembered because I ate there today: Anteprima. Anteprima serves some of the very best Italian food anywhere in Chicagoland. Just about everything I've had there has been superb, from the appetizers through the pastas and entrees right through to the desserts, and even their breads are pretty darn amazing. The service is friendly, knowledgeable, and accommodating. The décor/style is neighborhood bistro.

              The prices vary from fair to ridiculously low. You can view the dinner menu on their website at and you'll see that the a la carte prices are reasonable. If you can avoid Fridays and Saturdays, you can take advantage of their ridiculously low prix fixe deals - any three courses for $29 for dinner Sundays through Thursdays, and any three courses for $19 for their Sunday lunch 12:00-3:00.

              Anteprima is in the Andersonville neighborhood, seven miles north of the Loop. By public transportation from the Park Hyatt, you can get there in 30 minutes on the #147 CTA bus, 35 minutes on the CTA Red Line to the Berwyn stop including the 10-minute walk from there, or 45 minutes on the #22 CTA bus up Dearborn/Clark.

            2. re: extremepc

              Sunday Brunch suggestion:

              We went to a lot of great places last summer in Chicago, but one of my favorites was Brunch at Perennial Virant. You would need to grab a cab, but nice place.

              After eating , we took a short walk over to the zoo and the beach.