Chicago Travel Guide

Having lived in Chicago for 6 years, I was able to accumulate a list of all the great things to do and see and most importantly, eat. 

It’s always fun to have some kind of a guide to reference or at least help you get started before heading to a new city so here is mine on the great Chi town!


  • Bavettes Bar and Beouf – delish Steakhouse –BYOB. Super cool because you have to share a glass of wine with a random table (or your waiter) and someone could share one with you!
  • Etta- they pour wine into your mouth and delish food–It’s in Bucktown and near Paradise park- (a bar that’s on this list, too 😉)
  • Parlor Pizza– in the West Loop, which is a really popular area and full of newer restaurants. Great pizza and fun, busy bar scene, too
  • Bar Siena– in the West Loop, too. Great Italian
  • Sunda- Asian Fusion kind of restaurant that’s in River North
  • Piccolo Sogno– if it’s nice out, they have a great patio. Good Italian 
  • La Scarola- Another Italian place that’s near Piccolo Sogno– an old school Italian feel. Not too far from the West Loop area
  • GT Fish & Oyster– good seafood- more expensive
  • Joes Stone Crab- if you’re wanting to spend mula on some seafood
  • Duck Duck Goat- great Chinese food, cool restaurant and great drinks. Shared plates so go with a group!
  • Girl and the Goat– the chef was a top chef winner and it’s super popular– it’s all goat stuff
  • Summer House Santa Monica- in Lincoln Park and so cute. There’s also a pizza place attached that is so good. Both are good for dinner OR brunch/ lunch
  • Aba– new in the West Loop- Very cutesy and delish!
  • Gilt Bar– well known and great vibes
  • Maudes– classic in West Loop- great cocktails and mussels
  • Green Street Smoked Meats– BBQ in West loop.
  • Angry Crab– great casual spot for seafood, sauce or spice it up how you like


  • 3 Arts Café – cute spot to go for lunch/brunch. It’s inside Restoration Hardware in the Gold Coast area and so cute. Look up pictures, it’s adorable. You can also just get a coffee and walk around Restoration while you wait for a table
  • Hero Coffee– The cutest little hidden coffee shop on Jackson Ave in the Loop. Great spot for a photo and close to all the shopping on State street
  • Kanela– great brunch spot in Old Town and one in Wicker Park- I think there are more locations now, too
  • Au Cheval – hands down, the best burger. There’s usually always a wait but there is a bar across the street where you can hang while you wait and it’s def worth it. You can always go for breakfast/early lunch and get there right when it opens and the line tends to be shorter
  • Eataly- awesome place to see and lots of food options
  • Little Goat- the sister restaurant to Girl and the Goat but better for lunch 
  • Blue Door Café– there are two locations, one in Lincoln Park and one in the Gold Coast and they are both cutesy inside. The best Kale salad
  • Happy Camper- Pizza bar that’s really fun. It’s in the Old Town neighborhood that has a great street to just walk down with other bars and restaurants
  • Homeslice- Happy Campers sister restaurant and in Lincoln Park
  • Paradise Park- another one like Homeslice and Happy Camper (all 3 basically have the same menu since it’s the same owner)- in Wicker Park- they always decorate crazily for holidays!
  • Hash House a Go Go- they serve HUGE breakfast meals -it’s pretty fun. The chicken and waffles are huge and they put bacon in the batter
  • Portillos- Everyone in Chi loves this place.. it’s like a fast food restaurant but for Italian Beef
  • Lou Malnatis, Giodornos– deep dish pizza places
  • Beatrix – super cute spot for lunch or dinner
  • Big Star– Fun taco spot in Wicker Park- big open outside patio
  • BomboBar– really cool little drink spot that’s next to Bar Siena. They have awesome milkshakes and hot chocolates. Fun to get and take a picture 😉 
  • JoJo’s Milk Bar- good spot for desserts- fun grammable shakes! But also has food food


  • Cindy’s Rooftop- overlooks all of Millennium Park and the lake- great spot for a drink
  • The Violet Hour– if you’re willing to venture to Wicker Park (the hipster area) this is a cool, discrete bar.
  • Aviary– top notch cocktails
  • Three Dots and a Dash– underground tiki bar in River North that’s super cute and really cool. Fun drinks! 
  • Bub City– Fun little country bar in River North
  • Hub 51- bar in River North
  • Public House– another bar in River North that’s always fun
  • AceBounce– ping pong bar
  • Federales– bar in the West Loop and if you order a shot, they give it to you in an ice shot glass that you throw at a bell lol
  • The J Parker- very cute rooftop bar that overlooks Lincoln Park and the city. They have a cover for when it’s cold
  • London House– amazing views. Rooftop bar but you can go up there just to check it out
  • Punch Bowl Social- Next Door to Aba Restaurant and really cool inside! There are things to do like bowling and pool and all these other fun games (it’s huge) but also cute to just get drinks! 
  • Hampton Social- cutesy bar that has the neon sign that says ‘Rose all Day’ – also good for lunch!
  • RM Champagne Bar- really cute vibes in the West Loop- pretty inside to grab a drink and a cute patio for when it’s nice! 
  • Fight Club- dark but really cool- fun activity place to go out! 
  • Emporium- arcade bar- lots of fun old school games to play. Also have the ‘Don’t grow up it’s a trap’ neon sign.
  • Good Areas for night time bar scenes: River North, Old Town, West Loop. 

Sites to see:

  • Millennium Park– the bean
  • The Chicago Theater- on State Street- always fun to go get a good picture with it. It’s not far from the bean, so you could see both in the same day
  • Hancock Tower- just go up to the 95th floor and say you’re getting a drink and you can just go to the windows to look/take pics. The best view is definitely in the girls bathroom
  • Willis Tower- used to be the Sears Tower.. Similar to the Hancock but I am pretty sure you have to pay to get up there. They do have the glass floors though that you can walk out on and take cool pictures
  • Navy Pier- if it’s nice, great views but otherwise there’s not much there besides the ferris wheel 
  • Lincoln Park- The zoo here is free and it’s fun to walk through. The park is really pretty with great views, too.
  • North Ave Beach- if the weather is nice, this is the place to be. Always full of people and just a fun beach
  • Michigan Ave- Called the Miracle Mile and has all the shops. It’s fun to walk down but it is very touristy. The Water Tower is a little mall at the beginning of Michigan Ave, too. State Street also has a bunch of shopping and is a little less crowded than Michigan Ave
  • Wrigleyville- where the cubs stadium is and lots of bars. All along Clark street are the bars but they are very collegy.. meaning a lot of people are there to get DRUNK. (ha) But they’re fun to pop in and out of if you go to a baseball game! Otherwise, train it back to the city after the game and have dinner and go to bars there
  • Architectural Tour: This is super fun to do when the weather is nice! It sounds nerdy, I know but it’s actually amazing. It’s a boat tour along the Chicago river and highly recommended!

Live Music:

  • California Clipper
  • Kingston Mines
  • Green Mill
  • Schubas
  • Howl at the Moon


  • Revolution
  • Hopewell
  • Lagunitas 

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