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Highlights of Chicago

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Found this guide helpful

As a resident of the windy city for the past decade, I have taken a lot of time in getting to know all the amazing sides of Chicago. I hope to share some of my favorite spots and activities in the city to make your visit as pleasurable as possible.

Good for
  • Shopping Fanatic
  • Nature Lover
  • Foodie
  • Peace and Quiet Seeker
  • Beach Goer
  • Luxury Traveller
  • Like a Local

23 Places

4 City Tips

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Map

23 Places

The Magnificent Mile

Neighbourhoods, Points of Interest & Landmarks

Wrigley Field

Arenas & Stadiums

Girl & The Goat

Restaurants

The Publican

Restaurants

Edgewater Beach Cafe

Restaurants

Giordano's Pizza

Restaurants

Russian Tea Time

Restaurants

mana foodbar

Restaurants

Holy Name Cathedral

Architectural Buildings, Sacred & Religious Sites

North Avenue Beach

Beaches

Oak Street

Points of Interest & Landmarks

The Rookery

Architectural Buildings

Intelligentsia Coffee

Restaurants

The Magnificent Mile

Neighbourhoods, Points of Interest & Landmarks

Navy Pier

Piers & Boardwalks, Theme Parks

The Art Institute of Chicago

Art Museums

Millennium Park

Historic Walking Areas, Parks, Points of Interest & Landmarks

360 Chicago Observation Deck

Architectural Buildings, Observation Decks & Towers

The Magnificent Mile

Neighbourhoods, Points of Interest & Landmarks

Shedd Aquarium

Aquariums

Chicago Water Taxi

Ferries, Taxis & Shuttles

Signature Lounge

Jazz Clubs & Bars

Ritu N's City Tips

  • See the Magnificent Mile Light Fest during holidays & escape the frigid weather! Check out the Chriskindelmarket in Daley Plaza for a unique German experience in the city!
  • Come in the summer when the city comes to life...fests, beaches, and so many low cost outdoor activities can fill a 3 day visit easily!
  • When in chicago you must have Chicago style pizza and a chicago style hot dog!
  • Gratuity is usually included for parties of 5 or more. Other than that the standard tip ranges from 15 - 20%
  • Save
    The Magnificent Mile
    Neighbourhoods, Points of Interest & Landmarks
    See more photos
    Ritu N Says:

    Shopping wonderland! From Macys to Gucci to the Burberry Flagship store....everyones shopping needs can be met on the MAGNIFICENT MILE! Gorgeous lights in the winter and lake/river beauty in the warmer days really makes for a great activity.

    Good for
    • Luxury Traveller
    • Solo
    • Shopping Fanatic
    Tips
    • Gets crowded on the weekends, all year around.
    Plan to stay:/
    2-3 hours
    From the community
    Ranked #7 of 662 things to do in Chicago
    Certificate of Excellence 2014
    • Great Shopping! 21/10/2017
    • Shops 20/10/2017
    • The Magnificent Mile
    Address:
    North Michigan Avenue
    Chicago, IL 60611
    Phone:
    +1 312-642-3570
    Other:
  • Save
    Wrigley Field
    Arenas & Stadiums
    See more photos
    Ritu N Says:

    Sports fanatics love this place! The historical Wrigley Field. There is endless options for nightlife and food in the area to pair with a weekday or weekend game at the field!

    Good for
    • Like a Local
    • Solo
    • Friends
    • History Buff
    • Couples
    • Family
    • Nightlife Seeker
    Tips
    • There are often concerts held here in the summer too!
    Plan to stay:/
    2-3 hours
    From the community
    Ranked #5 of 662 things to do in Chicago
    Certificate of Excellence 2014
    • All that and more 21/10/2017
    • Baseball in October 20/10/2017
    • Wrigley Field
    Address:
    1060 W Addison
    Chicago, IL 60613-4397
    Phone:
    +1 773-404-2827
  • Save
    Girl & The Goat
    Restaurants (American)
    See more photos
    Ritu N Says:

    James Beard. Top Chef. Michelin. Name any major foodie accolade and this spot has it! Reasonably priced and a meal you will remember. Small plates and good for every dietary restriction.

    Good for
    • Foodie
    • Must See
    • LGBT
    • Trendsetter
    • Hidden Gems
    • Like a Local
    • Solo
    • Friends
    • Couples
    Tips
    • Book as far out as possible bc reservations here at a prime time are VERY HARD to come by!
    Plan to stay:/
    1-2 hours
    From the community
    Ranked #7 of 5,979 restaurants in Chicago
    Certificate of Excellence 2014
    • Looking for good options 20/10/2017
    • All the hype is the real deal 18/10/2017
    • Girl & The Goat
    Address:
    809 W Randolph St
    Chicago, IL 60607-2310
    Phone:
    +1 312-492-6262
    Price range:
    US$15 - US$30
    Hours:
    Sun - Thu
    16:30 - 23:00
    Fri - Sat
    16:30 - 00:00
    Other:
  • Save
    The Publican
    Restaurants (American)
    See more photos
    Ritu N Says:

    James Beard loves this place and so do meat eaters! The full pig to the octopus and everything in between is delicious! Their brunch is also quite noteworthy so check it out!

    Good for
    • Foodie
    • Friends
    • Couples
    • Trendsetter
    • Like a Local
    Tips
    • Small Plates. Meat focused. Brunch or dinner.
    Plan to stay:/
    1-2 hours
    From the community
    Ranked #120 of 5,979 restaurants in Chicago
    Certificate of Excellence 2014
    • Excellent Meal 17/10/2017
    • Good food, lively atmosphere 15/10/2017
    • The Publican
    Address:
    837 W Fulton Market
    Chicago, IL 60607-1318
    Phone:
    +1 312-733-9555
    Price range:
    US$25 - US$100
    Hours:
    Sun
    10:00 - 22:00
    Mon - Thu
    15:30 - 22:30
    Fri
    15:30 - 23:30
    Sat
    10:00 - 23:30
  • Save
    Edgewater Beach Cafe
    Restaurants (French, American, Seafood)
    Ritu N Says:

    This is a little serious hidden gem of chicago. Put your feet in the sand and enjoy simple and tasty food. You feel like you are not in the city! Outdoor seating on benches in the sand or on the concrete....a very unique spot in the north side of the city!

    Good for
    • Foodie
    • LGBT
    • Hidden Gems
    • Like a Local
    • Solo
    • Friends
    • Couples
    • Senior
    • Family
    Tips
    • Parking can be difficult but worth making the trip! Come when they have live music for a real outdoor treat!
    Plan to stay:/
    1-2 hours
    From the community
    Ranked #1,711 of 5,979 restaurants in Chicago
    • Charming atmosphere and good food 25/09/2017
    • My new favorite spot! 28/08/2017
    • Edgewater Beach Cafe
    Address:
    5545 N Sheridan Rd
    Chicago, IL 60640-1662
    Phone:
    +1 773-275-4141
    Price range:
    US$1 - US$20
    Hours:
    Sun
    08:00 - 19:00
    Mon - Sat
    11:00 - 23:00
    Other:
  • Save
    Giordano's Pizza
    Restaurants (Italian, Pizza)
    See more photos
    Ritu N Says:

    The best tasting chicago style pizza! Great balance of cheese, dough and sauce. The cheese is delightful and after 10 years in chicago, any of the locations meet our needs for a delicious Chicago Style pizza! The pizza does take 30 min at least to make, so this is not a quick bite!

    Good for
    • Foodie
    • Solo
    • Friends
    • Couples
    • Senior
    • Family
    Tips
    • Chicago style pizza! Well done. Cheese. or spinach or sausage. Never disappoints! Order your pizza in advance if you are in a rush!
    Plan to stay:/
    1-2 hours
    From the community
    Ranked #97 of 5,979 restaurants in Chicago
    Certificate of Excellence 2014
    • Did I say YUM 14/10/2017
    • Great food 13/10/2017
    • Giordano's Pizza
    Address:
    130 E Randolph St
    Prudential Plaza
    Chicago, IL 60601-6207
    Phone:
    +1 312-616-1200
    Price range:
    US$1 - US$20
    Hours:
    Sun - Thu
    11:00 - 23:00
    Fri - Sat
    11:00 - 00:00
    Other:
  • Save
    Russian Tea Time
    Restaurants (Russian, Eastern European)
    See more photos
    Ritu N Says:

    The first place in Chicago I went for an afternoon tea and it was delightful! The tea selection is great and so are the bites.

    Good for
    • Foodie
    • Peace and Quiet Seeker
    • Luxury Traveller
    • Trendsetter
    • Like a Local
    • Solo
    • Friends
    • Couples
    • Senior
    Tips
    • Located in the loop. Great afternoon trip option when staying downtown.
    Plan to stay:/
    1-2 hours
    From the community
    Ranked #163 of 5,979 restaurants in Chicago
    Certificate of Excellence 2014
    • Above Expectation! 20/10/2017
    • Always wanted to visit. 15/10/2017
    • Russian Tea Time
    Address:
    77 E Adams St
    Chicago, IL 60603-6113
    Phone:
    +1 312-360-0000
    Price range:
    US$20 - US$30
    Hours:
    Sun - Thu
    11:00 - 21:00
    Fri - Sat
    11:00 - 23:00
  • Save
    mana foodbar
    Restaurants (Spanish)
    See more photos
    Ritu N Says:

    When i bring my meat loving friends here, they are blown away by how delish the food is. The slider, for example, makes anyone think they are eating a meat burger but its 100% vegetarian with no meat flavors. Low key spot. A total hidden gem. No reservations but they do have outdoor seating! Small plates menu....so try a lot of stuff!

    Good for
    • Foodie
    • Solo
    • Friends
    • Couples
    • Hidden Gems
    • Like a Local
    Tips
    • No reservations. Put your name down and walk around a bit....there are a bunch of things to keep you busy in the area. Street Parking is usually easy to find too!
    Plan to stay:/
    1-2 hours
    From the community
    Ranked #666 of 5,979 restaurants in Chicago
    • Excellent food! 12/07/2017
    • Very good for Vegetarians!! 01/03/2017
    • mana foodbar
    Address:
    1742 W Division St
    Chicago, IL 60622-3229
    Phone:
    +1 773-342-1742
    Price range:
    US$15 - US$20
    Hours:
    Sun - Thu
    16:00 - 22:00
    Fri
    16:00 - 23:00
    Sat
    12:00 - 23:00
    Other:
  • Save
    Holy Name Cathedral
    Architectural Buildings, Sacred & Religious Sites
    See more photos
    Ritu N Says:

    Gorgeous cathedral. Worth a visit when in the city. Many love going to mass here and with the aesthetics of the place, its easy to see why!

    Good for
    • Thrifty Traveller
    • Solo
    • Friends
    • History Buff
    • Couples
    • Senior
    • Family
    • Art and Architecture Lover
    Tips
    • Gets crowded so get there early if you are going for any services.
    Plan to stay:/
    Less than 1 hour
    From the community
    Ranked #21 of 662 things to do in Chicago
    Certificate of Excellence 2014
    • Mass weekend of Marathon 18/10/2017
    • Beautiful cathedral 16/10/2017
    • Holy Name Cathedral
    Address:
    735 North State Street
    Chicago, IL 60654-3835
    Phone:
    +1 312-787-8040
    Hours:
    Sun
    06:30 - 19:00
    Mon - Fri
    05:30 - 19:00
    Sat
    07:30 - 21:00
    Other:
  • Save
    North Avenue Beach
    Beaches
    See more photos
    Ritu N Says:

    A fabulous oasis in the concrete jungle! There's Oak Street Beach too, but this one is bigger and closer to Lincoln Park to pair with the beach. Theres places to eat and just relax.

    Good for
    • Couples
    • Beach Goer
    • Family
    • Nature Lover
    Tips
    • food stands and drinks avail. Great spot to watch the Air & Water show
    Plan to stay:/
    2-3 hours
    From the community
    Ranked #81 of 662 things to do in Chicago
    Certificate of Excellence 2014
    • Too good a beach!!! 03/10/2017
    • Great Beach 10/09/2017
    • North Avenue Beach
    Address:
    1600 N. Lake Shore Dr
    Chicago, IL 60614
    Phone:
    312 747 0832
    Hours:
    Sun - Sat
    10:00 - 15:00
    Other:
  • Save
    Oak Street
    Points of Interest & Landmarks
    See more photos
    Ritu N Says:

    The the north end of Michigan ave is this high-end designer studded street. Take a stroll down Oat Street towards rush. Check out Hermes, Barneys, Jimmy Choo, and many more favorites for the shoppers!

    Good for
    • Foodie
    • Luxury Traveller
    • Like a Local
    • Solo
    • Friends
    • Couples
    • Shopping Fanatic
    Tips
    • Goto Fred's at Barneys for a nice bite while you are out shopping!
    Plan to stay:/
    1-2 hours
    From the community
    Ranked #142 of 662 things to do in Chicago
    • We just LOVE strolling up and Down Oak Street 25/08/2017
    • Upscale Shopping Mecca 16/08/2017
    • Oak Street
    Address:
    32 E Oak St # 200
    State St. to Michigan Ave.
    Chicago, IL 60611-1297
  • Save
    The Rookery
    Architectural Buildings
    See more photos
    Ritu N Says:

    Frank Lloyd Wright in the loop! What is better than that! Definitely a must see if you are into FLW work. If not the building is still work a minute of your time

    Good for
    • History Buff
    • Art and Architecture Lover
    • Trendsetter
    • Hidden Gems
    • Like a Local
    Plan to stay:/
    Less than 1 hour
    From the community
    Ranked #55 of 662 things to do in Chicago
    Certificate of Excellence 2014
    • Amazing Architecture with Limited Access 09/10/2017
    • Fabulous architectural site! 03/10/2017
    • The Rookery
    Address:
    209 S. LaSalle St.
    Chicago, IL 60604
    Phone:
    +1 312-994-4000
    Hours:
    Mon - Fri
    08:00 - 18:00
    Sat
    08:00 - 14:00
    Other:
  • Save
    Intelligentsia Coffee
    Restaurants (Cafe)
    Ritu N Says:

    One of the finest coffees in the country is roasted in the city of chicago! IF you need a coffee fix, hit up Intelligentsia coffee...you will NOT be disappointed.

    Good for
    • Foodie
    • Peace and Quiet Seeker
    • Hidden Gems
    • Like a Local
    • Solo
    • Friends
    • Couples
    • Senior
    • Family
    Tips
    • The Randolph Street location has nice sandwiches too!
    Plan to stay:/
    Less than 1 hour
    From the community
    Ranked #1,511 of 5,979 restaurants in Chicago
    • Good and pretentious coffee. But good. 04/10/2016
    • Coffee snobbery, but then it's great coffee 27/07/2016
    • Intelligentsia Coffee
    Address:
    3123 N Broadway St
    Chicago, IL 60657-4522
    Phone:
    +1 773-348-8058
    Price range:
    US$1 - US$20
    Hours:
    Mon - Fri
    06:30 - 21:00
    Sat - Sun
    07:00 - 21:00
    Other:
  • Save
    The Magnificent Mile
    Neighbourhoods, Points of Interest & Landmarks
    See more photos
    Ritu N Says:

    The south side (over the river) you will find parks, shopping (on state st) and museums. The north side if Michigan ave is known as the Magnificent Mile. Children go crazy for the American Girl store and all the beautiful tall buildings to the water tower, ghirardelli and hershey's stores! If there's precipitation, you can kill a lot of time in the city malls! On Michigan Ave there is a bunch of indoor shopping inside the Nordstrom building, Saks Fifth Ave building, Water Tower Place, and Bloomingdales building.

    Good for
    • Foodie
    • Must See
    • Luxury Traveller
    • Trendsetter
    • Solo
    • Friends
    • Couples
    • Senior
    • Shopping Fanatic
    • Family
    • Art and Architecture Lover
    Tips
    • Lots to do without spending a dime! Window shoppers paradise!
    Plan to stay:/
    2-3 hours
    From the community
    Ranked #7 of 662 things to do in Chicago
    Certificate of Excellence 2014
    • Great Shopping! 21/10/2017
    • Shops 20/10/2017
    • The Magnificent Mile
    Address:
    North Michigan Avenue
    Chicago, IL 60611
    Phone:
    +1 312-642-3570
    Other:
  • Save
    Navy Pier
    Piers & Boardwalks, Theme Parks
    See more photos
    Ritu N Says:

    This is a family favorite wonderland. From rides, to shopping to the IMAX there is something here for everyone. Take a boat ride around the city (esp the Architecture tours) or a water taxi to the museums. It feels like you are at a carnival and you can really spend an entire day here!

    Good for
    • Solo
    • Friends
    • Couples
    • Senior
    • Family
    Tips
    • From Memorial Day through Labor Day there are Firework shows on Wednesday night and Saturday night. They can be seen from the lakefront up til Belmont Harbor on a clear night!
    Plan to stay:/
    More than 3 hours
    From the community
    Ranked #35 of 662 things to do in Chicago
    Certificate of Excellence 2014
    • Love the activities and resto's with a beautiful view 21/10/2017
    • Well worth going out here 21/10/2017
    • Navy Pier
    Address:
    600 E Grand Ave
    Chicago, IL 60611-3419
    Phone:
    +1 312-595-7437
    Hours:
    Sun - Thu
    10:00 - 20:00
    Fri - Sat
    10:00 - 22:00
    Other:
  • Save
    The Art Institute of Chicago
    Art Museums
    See more photos
    Ritu N Says:

    Some of the best art in the country under this roof.

    Good for
    • Peace and Quiet Seeker
    • Art and Architecture Lover
    • History Buff
    Plan to stay:/
    2-3 hours
    From the community
    Ranked #1 of 662 things to do in Chicago
    Certificate of Excellence 2014
    • Spend Time With Treasures 21/10/2017
    • So much to see!! 21/10/2017
    • The Art Institute of Chicago
    Address:
    111 S Michigan Ave
    159 East Monroe Street
    Chicago, IL 60603
    Phone:
    +1 312-443-3600
    Price range:
    US$25 - US$25
    Hours:
    Thu
    10:30 - 20:00
    Fri - Wed
    10:30 - 17:00
    Other:
  • Save
    Millennium Park
    Historic Walking Areas, Parks, Points of Interest & Landmarks
    See more photos
    Ritu N Says:

    Who has not taken a picture in front of the "giant bean"? Its worth a trip to millennium park when in Chicago. You don't need much time if you just want to see the bean and get a pic. But its right in front of the lake and in the summer its quite delightful in this area.

    Good for
    • Must See
    • Thrifty Traveller
    • Solo
    • Friends
    • Couples
    • Senior
    • Family
    • Art and Architecture Lover
    Tips
    • no fees to get the pics!
    Plan to stay:/
    Less than 1 hour
    From the community
    Ranked #2 of 662 things to do in Chicago
    Certificate of Excellence 2014
    • A beautiful space! 21/10/2017
    • Beautiful park! 21/10/2017
    • Millennium Park
    Address:
    201 East Randolph Street
    Between Michigan Avenue & Columbus Avenue
    Chicago, IL 60601-6530
    Phone:
    +1 312-742-1168
    Hours:
    Sun - Sat
    06:00 - 23:00
    Other:
  • Save
    360 Chicago Observation Deck
    Architectural Buildings, Observation Decks & Towers
    See more photos
    Ritu N Says:

    With such a beautiful city, a nice view makes a trip complete. GO here and get your view needs in.

    Good for
    • Solo
    • Friends
    • Couples
    • Senior
    • Luxury Traveller
    • Family
    Plan to stay:/
    1-2 hours
    From the community
    Ranked #8 of 662 things to do in Chicago
    Certificate of Excellence 2014
    • Hold on to your lunch... 21/10/2017
    • wonderful views 21/10/2017
    • 360 Chicago Observation Deck
    Address:
    875 N Michigan Ave
    94th Floor
    Chicago, IL 60611-1803
    Phone:
    +1 312-751-3681
    Hours:
    Sun - Sat
    09:00 - 23:00
  • Save
    The Magnificent Mile
    Neighbourhoods, Points of Interest & Landmarks
    See more photos
    Ritu N Says:

    The north part of Michigan Ave. Children go crazy for the American Girl store and all the beautiful tall buildings to the water tower, ghirardelli and hershey's stores! If there's precipitation, you can kill a lot of time in the city malls! On Michigan Ave there is a bunch of indoor shopping inside the Nordstrom building, Saks Fifth Ave building, Water Tower Place, and Bloomingdales building.

    Good for
    • Must See
    • Luxury Traveller
    • Trendsetter
    • Solo
    • Friends
    • Couples
    • Senior
    • Shopping Fanatic
    • Family
    Tips
    • Walk it in the winter time for the beautiful holiday lights...or end the walk up the Mag mile into oak street beach!
    Plan to stay:/
    More than 3 hours
    From the community
    Ranked #7 of 662 things to do in Chicago
    Certificate of Excellence 2014
    • Great Shopping! 21/10/2017
    • Shops 20/10/2017
    • The Magnificent Mile
    Address:
    North Michigan Avenue
    Chicago, IL 60611
    Phone:
    +1 312-642-3570
    Other:
  • Save
    Shedd Aquarium
    Aquariums
    See more photos
    Ritu N Says:

    The first aquarium in the country! A must see for the aquatic lovers

    Good for
    • Must See
    • Thrifty Traveller
    • Solo
    • Friends
    • Couples
    • Family
    • Art and Architecture Lover
    • Nature Lover
    Tips
    • Take a water taxi! For a small fee ($7) you get a boat ride and your trip to Shedd is by water (bypass traffic). A win win :)
    Plan to stay:/
    More than 3 hours
    From the community
    Ranked #27 of 662 things to do in Chicago
    Certificate of Excellence 2014
    • Incredibly overpriced 21/10/2017
    • Went for a private function. Nice location and sights 19/10/2017
    • Shedd Aquarium
    Address:
    1200 S. Lake Shore Drive
    Chicago, IL 60605-2490
    Phone:
    +1 312-939-2438
    Hours:
    Mon - Fri
    09:00 - 17:00
    Sat - Sun
    09:00 - 18:00
    Other:
  • Save
    Chicago Water Taxi
    Ferries, Taxis & Shuttles
    See more photos
    Ritu N Says:

    Easy and scenic means to get around and have a water experience. Well priced and easy to access. When going to the museums or the willis tower, consider using the water taxi! Totally local style :)

    Good for
    • Thrifty Traveller
    • Hidden Gems
    • Like a Local
    • Solo
    • Friends
    • Couples
    • Senior
    • Family
    Tips
    • Wacker St Bridge or Navy Pier!
    Plan to stay:/
    Less than 1 hour
    From the community
    Ranked #1 of 34 Transportation in Chicago
    Certificate of Excellence 2014
    • Excellent trip and cheap. 18/10/2017
    • Quick transport with a view! 17/10/2017
    • Chicago Water Taxi
    Address:
    400 N. Michigan Avenue
    Chicago, IL 60611
    Phone:
    +1 312-337-1446
    Hours:
    Sun - Sat
    06:45 - 21:00
    Other:
  • Save
    Signature Lounge
    Jazz Clubs & Bars
    See more photos
    Ritu N Says:

    AN amazing view of the city! Great spot to have a drink and get one of the best views of the city. There will usually be a line in the summer so be prepared.

    Good for
    • Foodie
    • Must See
    • Luxury Traveller
    • Trendsetter
    • Solo
    • Friends
    • Couples
    • Senior
    • Family
    Tips
    • All year around...great spot!
    Plan to stay:/
    2-3 hours
    From the community
    Ranked #8 of 570 Nightlife in Chicago
    • Great view, not great service 16/10/2017
    • Afternoon drinks on a rainy day 12/10/2017
    • Signature Lounge
    Address:
    875 N Michigan Ave
    John Hancock Center
    Chicago, IL 60611-1803
    Phone:
    +1 312-787-7230
    Hours:
    Sun - Thu
    11:00 - 00:30
    Fri - Sat
    11:00 - 01:30
    Other:
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