Chicago Travel Guide || top five list

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So you don’t have enough time to do it all. Here is our take on our TOP FIVE haunts across Chicago if you are looking for an express tour, or just want to narrow it down. This is just our 2 cents on what we think you should absolutely put on the EAT | SEE | STAY list to get the best experience possible. Have fun exploring our handsome city.

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OK – we cheating a little bit here, but when a city has 25 restaurants with Michelin Stars you know there is a lot of good stuff going on. So we broke it down into different meals & of course drinks.



  • Black Dog Gelato – best gelato in town, get the salted caramel & mexican hot chocolate.
  • Glazed & Infused – Holy load of delicious handcrafted donuts. So sugary good, several locations across the city.
  • Hoosier Mama – A cute little storefront with delicious pies of all sorts. Take it to go – or snag one of the few tables for a slice. [R&H review]
  • Pleasant House Bakery – Alright this is pushing it, but I want to get it on the list. The best savory pies in the US hands-down. [R&H review]
  • Wow Bao – steamed asian buns filled with all sorts of deliciousness.


  • Big Star – the best ‘taco & marg’ in town. Do yourself a favor, catch the train downtown from ORD, get off at Damen, head across the street & kick-off your vakay starting here [R&H review], then taxi it to your accommodation. It will be the best welcoming to a city you can have.
  • Franks & Dawgs  – Elevated Chicago Hot-Dog’s, better tasting than Hot Doug’s because they make their own dawns in-house, the buns are delicious, and the sides are perfection [R&H review].
  • The Purple Pig– Good for Lunch or Dinner. Casual wine bar with incredible plates for sharing get the pig’s ear salad [R&H review]
  • Sable – Friendly service, slick room, great food to share & a fave place for a G&T – get the one with rosemary [R&H review]
  • XOCO – Rick Bayless is a legend when it comes Mexican Food. This casual eastern is a good way to sample his offerings [R&H review]


  • Alinea – It will send you home broke – but the guy is a genius. Fine-dining, so wear something fancy and be prepared to be blown away. It’s art on a plate.
  • Avec – Communal tables, plates for sharing, fabulous wine. It has been a staple & a fave for 10+ years. Don’t miss out. Go early if there are more than 2 of you to get a table.
  • Bavettes – Chicago is known for its steak house – this one we can always agree on – newish to the scene – but divine – french bistro style [R&H review]. If you must do traditional then we say Gene & Georgetti est. 1941.
  • Ruxbin – We take all our guests here. Casual elegance – we love it. They are constantly winning awards and the hearts & stomachs of everyone. Oh and it is BYOB. [R&H review]
  • Schwa – World best BYOB. Modern fine dining in a casual atmosphere [they play black sabbath]. Good luck booking [R&H review]


  • Aviary – Get a reservation online to avoid the lines. The most exquisite presentation & creations in the cocktail world. Not to be missed.
  • Billy Sunday – Fantastic bar, a delightful room to spend time in, and they serve really good food.
  • Signature Lounge – Best view in town – the cocktails are so-so but go for one drink just for the view. And pick off hours to avoid the crowds.
  • Three Dots & a Dash – If tiki was disneyland this would be the place. Great way to start the night with tiki drink to make you smile. It’s down an alley, and relatively easy to find look for the tiki torches.
  • Violet Hour – Beautiful velvet wrapped speak-easy cocktail bar with tasty craft cocktails.

Insiders tip: This is what the experts are currently listing as fave places to eat: Michelin & Eater.

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  • Architectural Boat Tour – A great way to see the city and the world’s original skyscrapers. It is restricted to weather, take a walking tour if you are brave enough to visit in the winter.
  • The Art Institute of Chicago – Our favorite is the Modern Wing, but do see the miniature rooms collection, and of course the text-book classic paintings, and admire the architecture too.
  • Lake Front / Lincoln Park – Lake Michigan is huge it truly looks like an ocean. Walk along the Lakefront from Oak Street to North Ave bridge and then wander thru Lincoln Park. Don’t miss the Studio Gang shelter, and the free Lincoln Park Zoo.
  • Millennium Park – Check out the gardens, the sculptures, the fountains & see a concert whilst enjoying a picnic in the warmer months. It is not considered a world-class park for nothing.
  • Wrigleyfield – Get some tickets in the bleachers, grab a beer before the game, munch on a Chicago Dog & watch the beloved Cubs, where they have been playing since 1916.


  • Chinatown Food Tour – Great way to see this part of the city, eat & learn along the way. Go hungry [R&H review].
  • The Driehaus Museum – WOW this is a magnificent home perfectly preserved in downtown chicago.
  • Farnsworth House  – A world-famous piece of architecture. I wish I could call it home – well a holiday home. [R&H review].
  • Osaka Japanese Garden – Located within Jackson Park it is a lovely spot for a picnic or to contemplate life.
  • Pullman District – Good for history & architecture buffs. You need to travel a little south, but amazing to step back in time to the hey-day of the railway.
  • Public Art Walking Tour – I am sneaking this one in – self guided – see Picasso, Miro. Chagall, Calder Kapoor etc.

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  • ACME Hotel – Reasonable prices, central location to all the ‘hoods. Modern and has a fun casual atmosphere.
  • The James Hotel – Smaller Hotel with a modern interior design, located downtown making it easy to get anywhere.
  • Park Hyatt Hotel – You can’t beat the location on the mag mile, and the views are pretty amazing too. Their spa has the best treatments, and Nomi is a great in-house restaurant / lounge.
  • Public – A little off the beaten path giving you a rest from the maddening crowds. Simple rooms.
  • The Thompson – a beautiful hotel with style & great on-site bar & restaurant [coming soon Dec 2013] also downtown.

Insiders tip: Chicago has decent transportation & taxi system with good prices. Locate yourself downtown, especially if you are a first timer, to make it easier to get anywhere in the city within 10-15 minutes. Book in advance & pre-pay for the best rates.

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ABOUT THESE GUIDES: We will be updating as things close/open, & our tastes change. You can see other Chicago Neighborhood Guides here.


4 responses to Chicago Travel Guide || top five list

  1. Mirja B. Neumann

    Hi Valentine, thank you for posting these recommendations. I’m planning on visiting Chicago next year and since I will probably only go for a weekend, this list is perfect! So excited to explore the city! Everybody seems to love Chicago.


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