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4 meals in Chicago (3 on a Monday)

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We will be spending one night and a full day in Chicago at the beginning of August.

We need a place for dinner on a Sunday evening somewhere between Midway Airport and Skokie where we'll be dropping our son off at a camp.

We'll be spending the following day in Chicago, so want great recs for breakfast, pizza for lunch, and a unique-to-Chicago dinner experience. Not too pricey, maybe $100 or less for 2 (with maybe 1 glass of wine for 1 of us). We could always swap that and have pizza for dinner if there is a great place for lunch. I realize Mondays can pose a problem, but I trust you Chowhounds know places that will be open on a Monday. (Actually it's probably a blessing, or I'd be making reservations at Charlie Trotter's and totally ruining our budget!)

Any and all help is appreciated. We've never been to the Windy City, and wish we had more time to spend. We want to make the most of our 24 hours!!

Thanks....

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  1. Head three miles south of the Midway Airport on Cicero Ave. and hang a right on W 79th St. to get to Chuck's Southern Comforts Cafe which is where I generally grab dinner when I arrive into Midway Airport.

    Chuck's serves an eclectic variety of cajun, BBQ, and Mexican/Latin foods and has a variety of daily specials.

    http://www.chuckscafe.com/

    Meals are generally in the $10-15 range excluding beverages.

    1. You might want to give us a little more guidance on where you will be in Chicago, types of cuisine you would like, etc. As to Sunday dinner, which I presume will include your son, I would suggest going to Greektown, which is just west of the Kennedy Expressway, near the Loop, and directly on your way from Midway to Skokie. Or, if you'd like to eat closer to Skokie, and your son is an adventurous eater, you could stop on Devon St. in the West Rogers Park area of Chicago for Indian food.

      2 Replies
      1. re: masha

        We have no idea where we'll be in Chicago. We've never been before. We're willing to drive anywhere for good food. As far as cuisines, I should have mentioned that; sorry. Husband doesn't like Indian or Thai. Anything else is fair game. Once I get a bunch of recs for food, then I'll figure out where to stay accordingly. Food first, then the hotel. Must have our priorities in order! :)

        Is Greektown the name of a restaurant or a section of the city? I'm assuming the latter. If so, what places do you recommend there? (We do all love Greek food.)

        1. re: wyf4lyf

          Greektown is an area of the City just west of downtown. My personal favorite there is Greek Islands but if you search the board you will find a lively debate on the best restaurant there. Santorini features fish, if that is more of interest. Pegasus has a rooftop garden, which can be lovely on a nice day.

          In terms of dinner on Monday evening, in the price range that you've set, there are should be a lot of choices. On the fine dining side, Custom House offers a prix fixe dinner, 3 course meal (5:00 pm & 5:30 pm seatings) for $46 every night. Marche, a French bistro-style restaurant, has a 3-course prix fixe dinner for $25 on Monday (and Wed.) evenings. For Mexican food, Frontera Grill is closed, but Salpicon is open; you'll be cutting it close on the price, but you should be able to stay within $50pp (before tax & tip). These are all relatively close to downtown. Once you get out into the neighborhoods, there are plenty of ethnic & other choices.

      2. Greektown is a great place to go. Rodity's is my favorite, a classic. Pegasus is a close second. Try Uno's pizza in downtown for a real taste of Chicago, an instution for 50 plus years. Sola restaurant is a great American Bistro in a real Chicago neighborhood. This is the link if you'd like to check it out. http://www.sola-restaurant.com/. Enjoy your short stay in Chi-town.

        1. A restaurant that I regret not going to more often is Sweets and Savories, which has a Monday deal that is $10 off their tasting menu and no corkage on BYOB. I think that this may push your $100 for two limit, but with BYOB and many courses (when I went, there were 8 courses) I thought it was a great value for what I felt was outstanding food and stellar service. Granted, it's been almost a year since I've been, but it was one of the most enjoyable meals I had last year.

          If you're looking for hustle and bustle atmosphere and a really vibrant area with lots of nightlife options around it, Sweets and Savories won't fit the bill. If you want a small, cozy place that makes you feel like you've just stumbled on a gem, enjoy.

          http://www.sweetsandsavorieschicago.com/

          1. We used to live in Chicago and LOVE the food there...and miss it, too! For a really fun lunch in Chicago, I'd say Ed Debevek's. It's part of the Lettuce Us Entertain You chain but is still just plain fun for lunch. Roller-skating waitresses, great burgers, world's smallest hot fudge sundae. We go there every time we return to Chicago (BTW...your son would love it if you could find a way to get him there with you. My boys both thought it was a blast!). Also downtown for dinner, if your husband is a big steak guy...you must go to the legendary Chicago Chop House. Classic great steaks (honestly some of the best I've ever eaten) and great steakhouse potatoes loaded with onions and garlic. You must go to the Original Uno pizzeria (don't forget a marker so you can sign your name on the wall). It's not fancy or pricey...but, a trip to Chicago wouldn't be a trip to Chicago without a stop at Uno. I would also echo the others recommendations for Greek Town...hard to go wrong there! Spiaggia is also a great restaurant but quite pricey. They do have a little bistro/cafe that is a bit less pricey and easier to get into. Nice view and great food there! If you're into ribs...Carson's has the classic old fashioned great ribs and a killer goldbrick sundae for dessert. One last thing...not a restaurant but DO NOT leave town without visiting a Garrett's popcorn shop (there are many locations). It's fresh, hot, buttery and downright sinful. our favorite is the Chicago mix...cheese and caramel together. Don't forget a pile of napkins...you'll need them. YUM! I'm getting hungry for it just typing this. Have fun!

            1. You need to have a Chicago dog and an Italian beef sandwich before you leave town. Portillos have several locations and a web site http://www.portillos.com. Also Hackney's have great burgers http://www.hackneys.net. I won't enter the pizza debate, but try a deep dish pizza. If you get the opportunity to go downtown take one of the many tours offered by the Chicago Architecure Foundation www.architecture.org. Enjoy your trip. I grew up in Chicago and think it is one of the world's great cities.

              1. I forgot about the Italian beef sandwiches and hot dogs, too! How will we fit it all in? We've signed up for a 10 a.m. CAF boat tour, so will probably go to Uno's for our pizza lunch. Maybe we'll get a hot dog for an afternoon snack? :)

                Great suggestions everyone! We have a big decision to make about dinner...so many options!