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Mar 26, 2009 05:56 PM

One Day in Chicago

So, I'm finally getting my day in Chicago. Problem is, it's one day! I'll be staying Friday night at the Hyatt Regency, then leaving from the Amtrak Station at 7 PM. If I only get one day, where MUST I go? Thinking more along the lines of holes-in-the-wall and cool market-type foodie destinations, as opposed to the high-end dining experience. Of course, we can probably do the high-end dinner thing Friday night.

What are your favorites?


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  1. Actually, correct me if I'm wrong, but it sounds like you have the opportunity for several meals: Friday dinner, Saturday breakfast, Saturday lunch, and Saturday dinner as long as you can get to Union Station by 7 p.m. (which is admittedly a serious constraint). I'm not saying you would necessarily want to have FOUR meals during your visit, but you can certainly have two and possibly three. Plus you also have the opportunity to pick up some of our local specialty foods with you to eat on the train. So it seems you can do far more than a single dinner!

    When you say Hyatt Regency, I'll assume you are referring to the Hyatt Regency Chicago on East Wacker Drive, and not to the ones at McCormick Place or near O'Hare Airport.

    There are so very many different cuisines at all levels, much of the answer to your request depends on exactly what YOU enjoy most. For example, if you WANT high-end dining, we have it; Alinea is the top table in town, considered by many (including Gourmet magazine) as the best restaurant in the entire country. It's a ten-minute cab ride from the Hyatt. Figure $300+ per person including wine/alcohol and tax/tip. If that's a bit rich for your blood, we have dozens of excellent contemporary American restaurants in the $100/pp range, the best of which IMHO are Cafe des Architectes and Aigre Doux, both of which are marginally walkable (3/4 mile) from the Hyatt. (Read more about our highest-end and casual fine dining restaurants at ). But there's SO much more here - steakhouses, seafood, every ethnicity imaginable, etc. So while I can come up with a sample itinerary - which I will do in a moment - it's easy enough to come up with other alternatives if there's some other type of food you love. Chinese? Thai? You name it, we have it! However, some types of food are easier to find in the downtown neighborhoods than others, and given your limited time here, you probably won't want to stray too terribly far and spend a lot of time in transit.

    If this were my first visit to Chicago, but I knew what Chicago has to offer, here's what I would do with an arrival on a late afternoon on Friday and a departure from Union Station on Saturday at 7:00 pm:

    FRIDAY NIGHT: Have a really nice dinner. As noted above, if you enjoy the highest-end places, go for Alinea ( ); it's a once-in-a-lifetime experience. If the price is too high, go to Cafe des Architectes ( ) or Aigre Doux ( ) for contemporary American fare.

    SATURDAY MORNING: When you get up, take the escalator inside the hotel down to Lower Columbus Drive (the level that has the entrance to the parking garage - it's below Upper Columbus Drive, the main arrival level for the hotel). Walk across the river on Lower Columbus 5 minutes to Fox & Obel. Fox & Obel is Chicago's premier gourmet food store, with the highest quality everything - fresh meats and seafood, cheeses, prepared foods, and baked goods. Some of their best baked products include their yummy cinnamon swirl rolls, the world's best bran muffins, excellent croissants, etc, as well as refrigerated pastries and such. You can get them all for carry-out at the bakery counter. Or, in the rear of the store is a cafe where you can get anything from a cup of coffee and a muffin to a complete meal, made to order. It's just your basic coffeehouse atmosphere, but the food is excellent. If the seating is crowded, there's more seating on the opposite side of the store. Get goodies to go for your trip, but don't overstuff yourself; you'll need to leave room to walk 10 minutes to...

    SATURDAY BRUNCH: Frontera Grill, one of the two Rick Bayless restaurants serving creative provincial Mexican food, is open for brunch on Saturdays. Ole! They open at 10:30 a.m. and I don't know how crowded they get for Saturday brunch; they don't take a lot of reservations because they keep most of the dining room open for walk-ins, and at most other times, you can expect a long wait to be seated. We locals generally know that you can walk right in and be seated if you arrive 10-15 minutes before they open the doors.

    STOP ALONG THE WAY: Go to one of the Loop locations of Garrett popcorn and get a big bag or tin for your trip. My personal favorite is their caramel popcorn with the roasted cashews in it, but I know one of their most popular varieties is the mixture of caramel popcorn and cheese popcorn.

    SATURDAY LATE AFTERNOON, EARLY DINNER: When in Rome... I mean... when in Chicago, this is your chance to get authentic Chicago-style deep-dish pizza. There are two main varieties. One is the single-crust "pizza in the pan" served by Pizzeria Uno and Pizzeria Due ( ) in River North, conveniently walkable in 5-10 minutes from the Hyatt and from Frontera, but a good 3/4 mile from there to Union Station. The other variety is the double-crust "stuffed" pizza served by Giordano's ( ), whose location at 223 W. Jackson is just a block or two from Union Station. Wherever you go, keep in mind that the pizza takes 30-45 minutes to bake; you can phone ahead with your pizza order so it's coming out of the oven when you walk in the door. Eat it there, or take it with you on the train; either way, the places are open all afternoon, so you can get some pizza right before you head off on your departure.

    If some of those choices aren't appealing to you, but there's some other kind of food you're hankering for, let us know what you're thinking, and we'll be happy to give you appropriate recommendations. Enjoy your visit!

    9 Replies
    1. re: nsxtasy

      What an great itinerary – thank you! I think we might just do exactly as you suggest. We love any food that is good product well prepared, from hot dogs to haute cuisine. Where's my best place for an awesome Chicago dog?

      1. re: lmariaschneider

        You can read a lot of opinions about the best place for Chicago hot dogs in the discussion at For a recommendation that's convenient to your other planned stops, Portillo's ( ) is a local chain that does very well at both Chicago hot dogs and our local Italian beef sandwiches, and they have a location on Ontario in River North, within walking distance of the Hyatt, Fox & Obel, Frontera Grill, and Uno/Due.

        Quick orientation - "The Loop" is our historical, commercial downtown area with tall office buildings, and is roughly a mile square, give or take. Union Station is roughly at the southwest corner of the Loop, and the Hyatt Regency Chicago is at the northeast corner of the Loop. The area immediately north of the Loop is on the other side of the Chicago River, which is why it is called River North; Uno/Due, that Portillo's, Aigre Doux, Cafe des Architectes, and Frontera Grill are all located in River North. Fox & Obel is north of the river but it's just east of the others, in an area sometimes called River East. With the exception of Alinea, every place I have mentioned here is within walking distance of both the Hyatt Regency Chicago and Union Station. You may want to leave your luggage at the hotel while you're walking all over, though. If you're looking to do some brief sightseeing in between food stops, just south of the Hyatt Regency is our new, beautiful Millennium Park, and just south of the park is the Art Institute of Chicago, our largest and most famous art museum. Tourist information is at

        1. re: lmariaschneider

          Luke's on W. Jackson is just a couple of blocks from Union Station and has very good dogs and fries. There's also a Gold Coast Dogs location inside the station (food court) but I vastly prefer Luke's.

          215 W. Jackson (at S. Wells St.)

          You could grab a meal and take it on the train.

          Others are not as impressed with the place as I am, but I used to work near there and ate there regularly. They have pretty good Italian beef too.

        2. re: nsxtasy

          Good suggestions. And, I could be wrong, but didn't Garrett's close?

          1. re: pastry634

            No, but I think I know why you think that. Garrett's has had several locations in the Loop for many years. They used to have a location on North Michigan Avenue, but they closed that one specific location a couple of years ago. A few months ago they actually opened a small location on Michigan near the old one for a couple months during the holidays, but that was strictly temporary. The other locations, including several in the Loop, are still in operation (and doing a big business).

            1. re: nsxtasy

              Oh, Ok, that makes sense. That makes me happy :) I always love to get my hands greasy on some of their cheesy popcorn.

              1. re: pastry634

                I spent quite a while this morning hoofing it around looking for the North St. Clair Street location, which I guess is the one that's gone. I'll try and find a location tomorrow. I want some for the train trip home!

                Thanks for the pointer to Fox & Obel. I got some wonderful cheese, a split of Chilean cabernet and a fresh baguette, and am having a decadent afternoon in my cheap Priceline room at the Fairmont. :-)

                1. re: lmariaschneider

                  There are a number of Garrett's in the Loop area. There is a big location on Randolph, next to the Oriental Theatre, where Rent is now showing. (not a free plug for Rent, they don't need it. just giving directions. ;-) )

                  1. re: ms. chow

                    I'm on my train home, munching on a big bag of Garrett's mix, which I find strangely delicious. We had an awesome brunch at Frontera, had a quick dog at Portillo's while waiting for our table at Frontera, and generally enjoyed your awesome city. It's like Manhattan but cleaner and with friendlier people.

                    Last night, we had dinner with a friend's daughter who recently moved to Chicago. She suggested a place called Nacional 27, which we enjoyed. Drinks and tapas were great, seafood paella was reasonably tasty for being not terribly authentic. We'll definitely be back for a long weekend soon, since we were really blown away by the cool vibe.

                    Thanks for the suggestions! I did end up at the Garrett's next to the theater where Rent is showing. :-)