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Chicago Itinerary Help

Hello to everyone and thank you for this wonderful forum. My BF & I will be arriving in Chicago on Sept 17 at 1:30 and taking the orange/ red line in from MDW to the Palmer. Could you give me feedback on this itinerary? Is it all "do-able"? Should I make reservations at any of the restaurants? No car, just public trans and walking (I love HopSpot.com). Thanks for all your help.

Thursday:
Check in, walk around Michigan Ave and parks
4:30ish Avec for dinner (to miss long waits)
7:00-8:30 Boat Tour from Mich Ave bridge
cocktails at Signatures
Portillo's for "combo wet hot and sweet" (I know it's not the best)
Bars along clark making way back to Palmer. Not sure where yet.

Friday:
11:30 - 2:30 Wicker Park Food Tour (Is it possible to get to Hot Doug's and back and still make it on time?)
LP Zoo by cab b/c zoo closes at 5:00 (will it be hard to catch a cab in WP?)
Spoon Thai for dinner around 8pm
Blues @ Kingston Mines or B.L.U.E.S.

Saturday:
8:30 ish Dim Sum at Shui Wah
Field Museum
MSI
Dinner @ Gage (semi-chosen for location) before fireworks at Navy Pier

Sunday:
Maxwell St Market for Mexican
To airport home

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  1. To the Palmer: Transfer at Roosevelt or just ride the Loop around to the Madison/Wabash stop.

    I'd skip the bars along Clark/Division as they are "suburbanite bars" and a bit dirty. The Rush triangle area is a bit nicer, but 40year old crowd. What kind of bars do you like? You might want to get some direction here.

    Hot Doug's isn't convenient to public transport. You can take the Western Buses up there, but you're better off taking a cab there, bus back (probably won't find a cab there). IIRC, HD's usually has a line, so be cautious of your schedule and make sure they'll have duckfat fries on the day you're going.

    Blues - I shy away from the Mines. Pops for Champaign is downtown and has music, Green Mill (way up north on the Red line) is awesome.

    1 Reply
    1. re: jfranci3

      Pops for Champagne. And no, it is not blues.

    2. Love the itinerary.

      Thursday - seems to work. Not sure what you mean by "Clark St." bars, but there are plenty of spots you can hit in the general State/Hubbard area (River North) just before you cross the Wacker bridge leading to the Loop and the Palmer House.

      Friday - what's this Wicker Park food tour you're planning? There are certainly good spots to eat in the area, but that all depends upon what you have planned. But I'm not sure that it sounds too exciting. As for catching a cab in Wicker Park, it is generally easy, although there will likely be fewer at around 5pm, just because most will still be downtown at that hour.

      Regardless, you can get to Hot Doug's before they open at 10:30 (Red Line train north to Belmont, Belmont bus west to California (just over 2 miles), walk north 1/4 mile to Hot Doug's. I'd get there by 10:15 to be safe (check out transitchicago.com and ctabustracker.com for help). Assuming you get there before they open, it should be easy to get to Wicker Park by 11:30 but you should call a cab to get there on time - then you can be there in about 10 minutes. FYI - they have duck fat fries on Fridays. hotdougs.com.

      Spoon Thai - excellent - I assume you have read this board and understand the differences between the translated Thai menu and the regular menu. If not, say so. Also, it's byo with liquor stores nearby. Finally, you might want to make a reservation or you could end up waiting a while.

      Saturday - sounds good . . . I like the Gage and it beats the hell out of eating at Navy Pier.

      Sunday - there are recs for food at the Market on this board . . . I assume you've checked those out?

      Any other help/suggestions needed?

      2 Replies
      1. re: BRB

        Cleaner route from the Palmer House to Hot Doug's. Take Blue Line (runs under Dearborn Street a block west of Palmer House) to California, stop is near Fullerton and Milwaukee. California bus north to Hot Doug's. Bus stop is across the street with northern turnaround in the next block north. Using the California bus back south to Milwaukee Avenue bus toward Wicker Park may be almost as fast and more reliable than getting a cab in the industrial area surrounding Hot Doug's. The open area immediately north of Hot Doug's used to hold a coal-fired Com Ed generating plant but is now mostly parking for Com Ed facilities and their tree trimming contractor.

        1. re: Eldon Kreider

          Didn't consider the Blue Line but that would be faster, and would also provide a better route to Wicker Park. To find out when the next bus will arrive, go to ctabustracker.com and click on the bus route (Kedzie/California - no. 52), direction of travel (north to Hot Doug's, south to Wicker Park) and the stop (likely California/Fullerton heading north and California/Roscoe heading south).

      2. Pops is not blues, nor is Green Mill. The Mines is good. How about Buddy Guys?

        1. Was your plan to eat at Hot Doug's and then do a "Wicker Park Food Tour" or were you thinking that eating at Hot Doug's was part of the "WPFT." I just wanted to clarify that Hot Doug's is not in Wicker Park.

          I love your other choices. All great examples of reasonably priced and wonderful food in the city. Have a wonderful trip.

          2 Replies
          1. re: chicgail

            Thank you so much everyone!

            As for "Clark Street bars", I just meant finding a bar for a few drinks on our way back to the hotel, while walking down Clark Street from Portillo's. And hell, we don't mind suburbanite, or necessarily dirty for that matter. And we're also 40ish, so low key neighborhood bars are fine; pool table a bonus; smoking permitted somewhere around it (I know Chic is all no smoking), even better. Will recheck the map, too. Thought Clark Street crossed the river into the loop. If not, I know there are lots of places on State/Hubbard.

            BRB, if you think we can make it back to Wicker Park after Hot Doug's, it's on (and I love you;-)! Public trans there and cab back. Will there be cabs in the area or will I have to call one? The Wicker Park Food tour is something I kind of wish I hadn't booked. It's an organized walking tour of WP food establishments. Probably playing on tourists fascination with Taste of Chicago (which, until reading these boards I, too, thought would be wonderful). Nonetheless, it's booked and I'm sure it will be fun.

            Yep, have the translated menu and recommendations for Spoon, and recommendations for everywhere else (these boards are awesome) and can't wait for the trip.

            Has anyone seen the ComedySportz (comedysportschicago) show that's playing midnights on Saturdays this month? It looks totally raunchy ala "The Aristocrats" so I didn't put a direct link here.

            Any other recommendations "while you're in/at..." would be would be much appreciated. Always trying to squeeze some other little fun or tasty thing in!

            Thanks again for your help!

            1. re: watermusic

              Clark definitely crosses the river into the Loop. Along your way from Portillo's, there's a Blue Chicago. Fado, if you are into Disneyland Irish. Frankie Z's next door to Frontera is def low-key and pool table. Boss Bar is also low key and pool table, although can get rowdy with overaged frat boys sometimes. English on La Salle is a fave. Crowd is more mid 20s to 30s, but they made a great Pimm's Cup in the summer.

          2. I'd suggest a late night taco run somewhere.

            2 Replies
            1. re: gordeaux

              Thank you EK and BRB re: Blue Line. Will check on that. And late night taco's sound good, too! Do they normally stay open late? Read somewhere about a place on Ashland, maybe? But the one on a certain side of the street and not the other?

              1. re: watermusic

                La Pasadita, east side of Ashland (not the ones on the west side of the street), carne asada. But if you're already going to the Maxwell St. Market, I wouldn't worry about LP.

            2. Any particular reason for cocktails at Signature aside from the view? I find their drinks very watered down, and pricey for what they are serving. If you are looking for roof top views, there's much more options such as the C bar at Affinia, the Terrace at Peninsula, the Roof at Wit, or the bar at Trump Tower.

              3 Replies
              1. re: ms. chow

                Tru dat on the roof top bars. In my opinion, being on a mid level building is better than the highest. The views are better. Being in the higher buildings is the same as looking down from an airplane, which doesn't feel as special. Since it is new and hip, the line at the Wit has been noteable.

                I'd email the Wicker Park tour people and let them know you'll be missing the first stop, which is a hot dog stand anyway (not a particularly prominent one at that)

                1. re: ms. chow

                  Ms Chow-Signatures was just for the view. Would you recommend one of those other in particular (and in the same area)?

                  1. re: watermusic

                    I echo jfranci3's comment. At a giant skyscraper like Hancock, the view is more like view from an airplane. You get a great panorama of the lake, the city etc, but everything looks like ants. At a mid-level skyscraper, the views are of the city. Personally i feel more connected that way.

                    Anyway, this is your vacation, so it is about you. If the view at Signature is what you are after, go for it. My only opinion is that the quality of the cocktails does not justify the price they charge. if i have to pick one from the places i've mentioned, Roof would be my choice. Although it is in the Loop.