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The Ultimate Chicago Travel Guide

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I have been in Chicago for nine years – and I have FINALLY gotten around to creating the ultimate Chicago Travel Guide! Here is a list of where to stay and eat, plus the best events, music festivals, museums, and things to do. Use this list to plan a vacation or if you live in Chicago use it to inspire you to explore new parts of the city.

Where to Stay

Loews Hotel – A new hotel right in the Loop that is fitting for both business travelers and tourists. The hotel boasts some of the best views downtown Chicago architecture.
Ambassador Hotel – A charming boutique hotel in the Gold Coast, one of Chicago’s prettiest neighborhoods.
The Langham – A Forbes 5 star luxury hotel downtown with an exceptional restaurant on site.
Soho House – Right in the West Loop in the middle of some of the best restaurants in the city.
Hotel Zachary – Starwood’s long-awaited addition to Wrigley, a perfect place to stay if you are heading to a Cub’s game.

Can’t Miss Restaurants

Avec – A shared plates restaurant in the West Loop that you should put on the top of your list of Chicago restaurants to visit. Be sure to try the chorizo stuffed dates.
Blue Door Kitchen – This restaurant is owned by Oprah’s former personal chef, and it has a garden patio and fried chicken.
Au Cheval – The burger is the most amazing burger I have tasted – the wait can be up to 5 hours long so I recommend going late night.
Osteria Langhe – Authentic pastas from the Piedmonte region of Italy.
3 Arts Café – A stunning restaurant in the new Restoration Hardware that serves perfectly executed American food.
Bavette’s Bar and Boeuf – My favorite spot for steaks, and the chocolate pie is legendary.
Publican – One of Charles’s favorite restaurants, they have a brunch men can get on board with, and an always changing dinner menu.
Bar Siena – Fabio Viviani’s casual Italian restaurant in the West Loop that serves pizza and pasta.
Longman and Eagle – It is worth the trip to Logan Square for this impossibly cool restaurant. Just get there early since they do not take reservations.
Balena – An Italian restaurant in Lincoln park with a rustic romantic atmosphere. It is a favorite among locals and we often go there for special occasions. I love their homemade pastas.
Alinea – The number one restaurant in America gives patrons an incredible dining experience, just get tickets away in advance.
Duck Duck Goat – Top Chef and Iron Chef champion Stephanie Izard’s newest restaurant serves dim sum that is so good you will want to go back for more.
Schwa – Consider yourself lucky to get a reservation, Schwa is hard to get into because it is one of the most respected restaurants in Chicago. Expect a 9-course meal that will blow your mind. Don’t forget – it is BYOB.
Big Star – A taco joint with a large patio for some of the best people watching in the city. The tacos are some of the best in the city too.
Dove’s Luncheonette – A diner where you can add a fried egg to anything on the menu.
Cindy’s Rooftop – This rooftop restaurant with views of Grant Park and Lake Michigan is the best place to go for family style brunch, or for cockails and views of the fireworks on Wednesdays and Saturdays during the summer.
Doughnut Vault – This small doughnut shop started Chicago’s doughnut crazy. They are known for old fashioned styled doughnuts.
Stan’s Doughnuts – Stan’s has a few locations in Chicago, and I think it is just as good as doughnut vault (but more conveniently located).
The Bristol – An American restaurant with European influences, The Bristol has homemade pasta, and outstanding meat dishes like the pork shank which is pictured above.
Davanti Enoteca – An Italian restaurant in Little Italy with the best cacio e pepe in the city.
Roister – A sister restaurant to Alinea that has a completely different vibe. Expect 90s rap music and an affordable meal you won’t forget. Order the chicken three ways and you won’t regret it.
Mindy’s HotChocolate – Mindy is a Chicago legend, and her restaurant serves up one of the best brunchs in Chicago. Be sure to get some cookies to go too.
Summer House Santa Monica – A bright sunny restaurant where it always feels like summer in my favorite part of Lincoln Park. The menu is a nod to California with healthier fare and items like salmon burgers, tacos, and avocado toast. The restaurant also has an epic bakery that you should not miss.
RPM Italian – A formal Italian restaurant and an ideal place to dine before the theater.
The Purple Pig – A small plates restaurant on the Magnificent Mile with inventive Mediterranean food and a lively atmosphere.
Sepia – A fine dining restaurant in the West Loop fitting for a special occasion.

Where to Get Drinks

Green Door Tavern / The Drifter – One of the oldest bars in Chicago. Go down to the second floor and you will find The Drifter, a small cocktail lounge.
Untitled – An underground speakeasy style bar with live music, burlesque performances, and great drinks.
RM Champagne – A champagne bar and cocktail lounge with a patio in the West Loop.
Old Town Ale House – A dive bar across the street from Second City. Heads up – it is cash only.
Three Dots and a Dash – An underground tiki bar in River North that serves tiki and large format cocktails.
Parson’s Chicken and Fish – The patio is the best place to hang out on a summer day, and their negroni slushies are one the best summertime cocktails in Chicago.

What to Do

Architectural Boat Tour – This is one of the best ways to see Chicago and learn a bit about the city’s history. Book ahead!
Ferris Wheel – Did you know that the Ferris Wheel made it debut at the Chicago World’s Fair? Last year Chicago’s Ferris Wheel on Navy Pier got a major upgrade and offers wonderful views of Lake Michigan and the skyline.
Kayak in the Chicago River – You can rent kayaks from a company off Chicago Avenue if you want to kayak in the Chicago River.
Rent a Boat – There are boat rental companies that let you rent small party boats to cruise the river, or bigger boats for partying in the “playpen” a section of Lake Michigan that turns into a daytime party during weekends in the summer.
Go to the top of the Hancock Building for drinks at the Signature Room – I recommend having a cocktail at the Signature Room at the Hancock Tower instead of going to the top of the Sear Tower (now called the Willis Tower).
Bike the Lake Front Path – Chicago has a bike share program and miles of beautiful bike paths along the lake.
See a show at Second City – This is a must! Many famous comedians and SNL cast members got their start at Second City and it is always tons of laughs.
Cheer for the Cubs at Wrigley – This is also a must (assuming it is baseball season and the cubs are in town). If you want a rowdier experience get tickets for the Bleachers.
Take in a Blackhawks Game – Chicago LOVES the Blackhawks and going to a game is a really fun experience even if you are not a hockey fan.
See a Bulls Game – I must admit that I haven’t done this yet, but it is at the top of my list!
Shop on the Magnificent Mile – Expect to find big national retailers and luxury designer goods. It can be crowded on weekends.

Chicago Events

Chicago Gourmet – A weekend long event that takes over Millenium Park. Chicago Gourmet is a complete foodie experience with live cooking demonstrations from celebrity chefs, wine tastings, and bites from dozens of Chicago restaurants.
Air and Water Show – This is a love it or hate it event… and I don’t love it. It is a chance to see jets buzz through the city on the third weekend in August.
Taste of Chicago – An event that takes over Grant Park for five days in July with food tastings from Chicago restaurants and live music.
Pride Weekend – Pride is a full weekend long festival packed with events taking place in June. The parade in Boystown is the main event.
Chicago Marathon – The city is pretty flat, so it is an easier course.
St. Patrick’s Day – Chicago is so into St. Patrick’s Day that we dye our river green, and then party all weekend long.
Summer Festivals – There is a street fest or food festival every weekend in the summer ranging from taco fest and rib fest to garden walks.
Christkindlmarket – A German Christmas market takes over Daly Plaza from mid November until Christmas Eve.
Zoo Lights at the Lincoln Park Zoo – The zoo goes all out when it comes to decorating for Christmas, and admission is free.

Music Festivals

Lollapalooza – This is the ultimate four-day multi-stage festival that attracts major music acts.
Pitchfork – Some call this Lolla’s little sister, it is smaller and more chill and features more emerging artists.
Lakeshake – A three-day country music festival on Northerly Island.
Windy City Smokeout – A celebration of country music and barbecue, some people go just for the food.
Spring Awakening – Chicago’s EDM music festival in June.
Mamby on the Beach – As the name suggests, this takes place on the beach and features a wide range of music.
Chicago Blues Fest – A three day festival in Millennium Park – and admission is free!
North Coast Music Festival – This takes place over Labor Day weekend in the West Loop and attracts acts like Deadmau5.
Riot Fest – The last big festival of the summer takes place in September and tends to feature more punk and rock performers.


Chicago History Museum – This small museum in Old Town is fun and family friendly. It’s the best place to learn all about Chicago.
Shedd Aquarium – Chicago has an excellent aquarium, and they host Jazzin at the Shedd, a cocktail party with live jazz and views of the Navy Pier fireworks on Wednesdays during the summer.
Art Institute of Chicago – One of the best art museums in the world, the permanent collection is outstanding with large collections of both Impressionist and Modern Art, and the museum also attracts large traveling exhibitions.
Field Museum – An ideal place to take kids on a rainy day this museum has a little bit of everything, including Sue, a massive skeleton of a T-Rex.

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