Help a Reader Travel: Chicago

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Welcome to another post of helping a reader travel! As I’ve mentioned before, I have not been to every destination (unfortunately), but do get questions from friends and other blog readers on all sort of travel destination questions. Thus far, we’ve been able to help other readers travel to Maui, The Greek Islands, Pacific Coast Highway, Argentina, Costa Rica, Cape Cod & The Islands, Iceland, Geneva, Canadian Rockies, Rome, Israel, Peru, Las Vegas, and Stockholm.

So this weeks travel destination includes Chicago. I received the following email from reader Mike:

“With the Fall coming up, I’ve been looking for a weekend getaway with my girlfriend to Chicago. We’ve never been, so would love some help. What area would you recommend staying and any particular hotels? Also, what activities would you suggest? I also know there are some great restaurants in Chicago, so any help there would be great. Your help is much appreciated!”

I’ve been to Chicago a bunch for work, but only once for a more leisure trip.  Chicago is a really cool city. We were staying with friends so went along with their weekend plans. We did, however, go on the Architecture Tour which I’d recommend. It cost about $30 per person and is a one hour boat cruise that goes through the Chicago River. The day we went (late October) was incredibly cold, so I’d recommend this tour on a nicer day out, if possible. If not, just bring a hat and gloves. Make sure to get deep dish pizza too! But be prepared that it takes awhile.

If you’ve been to Chicago, let’s help out reader Mike by commenting below. Also, if you have any upcoming travel where you need some help, feel free to email me at to be a featured “Help a Reader Travel” Monday special. Thanks!

The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.



  1. Where to start…

    Deep Dish Pizza: Lou Malnati’s (Gold Coast area)
    Fine Dining: Alinea. NEXT. (Modern; dinner; both will need to be booked well in advanced; costly).
    Other Restos that can’t go wrong: Coast (Japanese; dinner). Le Creperie (French; dinner/brunch). Mindy’s Hot Chocolate (American; brunch). M Henry (American; Brunch)

    Great Neighbourhoods (lots of bars/restos): Wrigley (Cubs area), Wicker Park/Bucktown

    Stay away from (tourist traps): Navy Pier, Michigan Ave (unless you have something very specific you’re looking for. Shops you’ll see can be found at any mall, i.e. Banana Republic, Best Buy, Bloomingdales, Macy’s)

    There’s so so much more…but this is what I can think of off the top of my head.

  2. Start looking on Groupon. They offer lots of good tourist activities at 50% off in Chicago. Since Chicago is the headquarters of Groupon, it has many more deals than many other cities. Since you have some time before you travel, you may be able to snag some good deals.

    Food. Lou Malnatis is a MUST for deep dish pizza.

    Cabs are cheaper than many other cities (like NY), but they can still get pricey, so I would stay downtown, near the Gold Coast or Michigan Ave. Yes Michigan Ave is a tourist trap, but pretty close to everything.

    My favorite hotel is the Wit by Doubletree. They also have a great rooftop bar called The Roof @ the Wit. Some other nice hotels are the Dana Hotel, Radisson Blu, Swissotel, Ivy Hotel. There are many more too.

  3. 1) If you like steaks – goto David Burke’s Steakhouse. It is pricey, but it is the best steak (maybe a tie for Peter Luger’s in Brooklyn) I’ve ever had.
    Also ask for a tour of the room where they dry age their beef. If you know anything about aged beef, it’s interesting.

    2) stay downtown. If you need to take a cab outside city limits, it’s fare and a half because city cabs aren’t allowed to pick up passengers outside off city limits.

    3) there are a lot of nice hotels. Downtown I’ve only stayed at the Palmer House (Hilton). It’s old school fancy (was a big hotel for stars in the 30s-50s), but recently renovated. The elevators are horrendous, but if you’re gold/diamond, you can get access to the “VIP” elevator.

  4. I’ve traveled weekly for work for the last 5 years and Frontera Grill is my favorite restaurant anywhere in the country. Just incredible Mexican food – the way you dream of it tasting.

    I’ve stayed at about 20 Chicago hotels and my favorites are the Drake (for an old school Chicago feel, and the best hotel breakfast I’ve had anywhere) and the Swissotel (for a new/chic experience).

  5. Hotels: I’m partial to the Renaissance Blackstone on South Michigan Avenue. If you’re looking to save money, I’ve had good success with Priceline – often getting the Hyatt on Wacker.

    Transportation: Don’t rent a car! Having a car in the city is more hassle and expense than it is worth. If you are flying or training in, utilize public transportation and cabs. I recommend the three day all you can ride pass – which you can get now for $9 on groupon (they mail them to your house).

    Restaurants: You can’t swing a cat in Chicago without hitting a good restaurant. There are a lot of really interesting ethnic neighborhoods with authentic restaurants – any cuisine you could want from Polish, to central African, to Korean.

    Theater: Chicago has an awesome theater scene. sells half-price day-of tickets at its outlets on W Randolph in the loop and at the Water Tower. There are a lot of great, local theater companies doing some really interesting things — everything from traditional Shakespeare to experimental horror.

  6. I rate the The James (, and Public ( as great boutique hotels.

    @Brent’s suggestion on Priceline is valuable. I’ve done it a couple of times and he’s right, Hyatt does come up frequently.

  7. Awesome restaurants in Chicago! We are planning on dinner at Schwa next month. It’s supposed to compare to Alinea in quality of food but is different in all other ways. It’s difficult to get reservations. But a lot of the gastro pubs in Chicago don’t take reservations (which can be a good thing since some of the best restaurants book 3 months in advance). Try Longman & Eagle (incredible food) and the Purple Pig. Neither require a reservation. Also Girl and the Goat is wonderful but you need to go right when they open unless you can somehow book a table in advance. Enjoy! I love Chicago’s food!

  8. My favorite activity, the signature lounge at the john hancock.

    Many tourists pay ~$20 to go to the observation deck of sears tower or john hancock. While these are great experiences, i prefer the signature lounge at the 96th floor, specially if you are an adults only group. First, it is FREE to get in. Second, it is a bar with nice sitting areas and beautiful views, open late. They have overpriced food and beverages (but remember you are paying for the view). Go at sundown to see the city lights lit up. If you feel like fine dinning, they have a restaurant on the 95th floor, make reservations, expensive, Dress Formal.

  9. I had an amazing meal at Girl and the Goat (by Top Chef Winner, Stephanie Izard). I also just read the book Life, On the Line by Chef Grant Achatz and it has made me want to try Alinea and Next more than anything in the world! But they do their reservations based on a ticketing system, though they sometimes make tickets available on their Facebook pages I’ve seen!

  10. I was born in the Windy City but still prefer Colorado. I agree with the Frontera Grill but avoid R.B. other restaurant since I was there in December and had a terrible high price, poor service, and mediocre food(one of the worst restaurant experiences I have ever had). Shame on the R.B restaurant. The Art Institute is always a winner and easy to get to. If you stay near Michigan then public transport is easy and go on the the Chicago transit website. I also recommend the architectural tour!

  11. In June, I had a conference in Chicago. We split our time between the Hyatt Regency and the Conrad. We paid for the Hyatt and used points for the Conrad. amazing experiences at both

  12. Had some great food at The Girl and the Goat, Publican, Aria, 312 Chicago (half price wines Sunday night), and Giordanos pizza. The Art Insitute is awesome! So is Millenium park-they have great open air exercise in the warm weather on Saturday morning and outdoor dance lessons Friday night-both are free and a lot of fun. Not sure if the season is over, but you can sometimes catch free rehearsals for the evening music concerts at the park. We also took a Chicago Greeters tour(also free )!if you book a couple of weeks in advance, they will customizema tour to your interests. LOVE Chicago

  13. Don’t rent a car when you go to Chicago. You can take the “el” (the city above ground subway) from either MDW (Orange Line) or ORD (Blue Line) into the loop (downtown). Use Google Maps to plot out easy directions via mass transit. The CTA bus system is good as well, no safety concerns during the day when I’ve used them, and I have a lot of city friends who tell me it’s typically fine all hours.

    I highly recommend the Shedd Aquarium and the Chicago Museum of Art for interesting destinations, but Shedd can get quite busy, so go early.

    If you are into craft beer, check out Goose Island Brewery. If you’re into really good food and really good bourbon, check out the restaurant/bar/overnight venue called Longman & Eagle. If you want the absolute BEST breakfast in town, check out The Bongo Room. There are 3 locations and they are all very busy (expect a 30-45 minute wait), but it is worth every minute on your feet. I make a point to go there every time I am in the city. I adore Chicago and wish it could be where I call home someday.

  14. Just came back from our first visit,highly recommend the Bull and Bear, 431 N Wells St. Don’t let it being a tavern fool you the food is amazing. When I first saw the menu and that lots of choices were organic I was a little worried. We had the Kobe Burgers, french fires with gruyere cheese, the Mediterranean plate(homemade hummus and a bol of the mac and cheeses. Yummo! Go by the Drake and go to the Cape Cod room too. Signature lounge was awesome-but overpriced!

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