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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 Traveler
  • Like a Local

23 Places

4 City Tips

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Map

23 Places

The Magnificent Mile

Neighborhoods, Points of Interest & Landmarks

Wrigley Field

Arenas & Stadiums

Girl & The Goat

Restaurants

The Publican

Restaurants

Edgewater Beach Cafe

Restaurants

Giordano's

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 Building

Historic Sites, Architectural Buildings, Points of Interest & Landmarks

Intelligentsia Coffee

Restaurants

The Magnificent Mile

Neighborhoods, Points of Interest & Landmarks

Navy Pier

Theme Parks, Piers & Boardwalks

The Art Institute of Chicago

Art Museums

Millennium Park

Parks, Points of Interest & Landmarks, Historic Walking Areas

360 Chicago Observation Deck

Points of Interest & Landmarks, Architectural Buildings, Observation Decks & Towers

The Magnificent Mile

Neighborhoods, Points of Interest & Landmarks

Shedd Aquarium

Aquariums

Chicago Water Taxi

Ferries, Taxis & Shuttles

Signature Lounge

Jazz Clubs & Bars

RituandTim'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%
  • The Magnificent Mile
    Neighborhoods, Points of Interest & Landmarks
    See more photos
    RituandTim 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 Traveler
    • Solo
    • Shopping Fanatic
    Tips
    • Gets crowded on the weekends, all year around.
    Plan to stay:
    2-3 hours
    From the community
    Ranked #4 of 647 things to do in Chicago
    Certificate of Excellence 2014
    • Magnificent! 12/12/2018
    • Great, free fun! 12/11/2018
    • The Magnificent Mile
    Address:
    North Michigan Avenue
    Chicago, IL 60611
    Phone:
    +1 312-409-5560
    Other:
  • Wrigley Field
    Arenas & Stadiums
    See more photos
    RituandTim 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 #16 of 647 things to do in Chicago
    Certificate of Excellence 2014
    • You Have To See A Game Here 12/12/2018
    • It's called the friendly confinds for a good reason! 12/11/2018
    • Wrigley Field
    Address:
    1060 W. Addison St.
    Chicago, IL 60613-4566
    Phone:
    +1 773-388-8270
    Price range:
    $25 - $25
    Other:
  • Girl & The Goat
    Restaurants (American)
    See more photos
    RituandTim 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 #5 of 6,267 restaurants in Chicago
    Certificate of Excellence 2014
    • Amazing dining 12/13/2018
    • Fabulous dining experience 12/12/2018
    • Girl & The Goat
    Address:
    809 W Randolph St
    Chicago, IL 60607-2310
    Phone:
    +1 312-492-6262
    Price range:
    $15 - $30
    Hours:
    Sun - Thu
    4:30 PM - 11:00 PM
    Fri - Sat
    4:30 PM - 12:00 AM
    Other:
  • The Publican
    Restaurants (American)
    See more photos
    RituandTim 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 #237 of 6,267 restaurants in Chicago
    Certificate of Excellence 2014
    • Good and experimental food (even for vegan) 12/10/2018
    • All about the pickles! 12/01/2018
    • The Publican
    Address:
    837 W Fulton Market
    Chicago, IL 60607-1318
    Phone:
    +1 312-733-9555
    Price range:
    $25 - $100
    Hours:
    Sun
    10:00 AM - 10:00 PM
    Mon - Thu
    3:30 PM - 10:30 PM
    Fri
    3:30 PM - 11:30 PM
    Sat
    10:00 AM - 11:30 PM
    Other:
  • Edgewater Beach Cafe
    Restaurants (French, American, Seafood)
    RituandTim 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 #1,997 of 6,267 restaurants in Chicago
    • Fantastic food in a classy place, not too expensive 09/07/2018
    • Not for vegeterians! 11/23/2017
    • Edgewater Beach Cafe
    Address:
    5545 N Sheridan Rd
    Chicago, IL 60640-1662
    Phone:
    +1 773-275-4141
    Price range:
    $1 - $20
    Hours:
    Sun
    8:00 AM - 7:00 PM
    Mon - Sat
    11:00 AM - 11:00 PM
    Other:
  • Giordano's
    Restaurants (Italian, American, Pizza)
    See more photos
    RituandTim 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 #265 of 6,267 restaurants in Chicago
    Certificate of Excellence 2014
    • Pizza best pizza in town 12/11/2018
    • Delicious Pizza! 12/06/2018
    • Giordano's
    Address:
    130 E Randolph St
    Prudential Plaza
    Chicago, IL 60601
    Phone:
    +1 312-616-1200
    Price range:
    $1 - $20
    Hours:
    Sun - Thu
    11:00 AM - 11:00 PM
    Fri - Sat
    11:00 AM - 12:00 AM
    Other:
  • Russian Tea Time
    Restaurants (Russian, Eastern European)
    See more photos
    RituandTim 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 Traveler
    • 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 #181 of 6,267 restaurants in Chicago
    Certificate of Excellence 2014
    • Great location for pre-opera or pre-symphony meal and it has a unique ambiance and menu. 12/03/2018
    • When in Chicago...don't miss this! 11/26/2018
    • Russian Tea Time
    Address:
    77 E Adams St
    Chicago, IL 60603-6113
    Phone:
    +1 312-360-0000
    Price range:
    $20 - $30
    Hours:
    Sun - Thu
    11:00 AM - 9:00 PM
    Fri - Sat
    11:00 AM - 11:00 PM
    Other:
  • mana foodbar
    Restaurants (Spanish)
    See more photos
    RituandTim 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 #504 of 6,267 restaurants in Chicago
    • Surprised at how good Vegan could be 07/11/2018
    • An absolute must! 03/31/2018
    • mana foodbar
    Address:
    1742 W Division St
    Chicago, IL 60622-3229
    Phone:
    +1 773-342-1742
    Price range:
    $15 - $20
    Hours:
    Sun - Thu
    4:00 PM - 10:00 PM
    Fri
    4:00 PM - 11:00 PM
    Sat
    12:00 PM - 11:00 PM
    Other:
  • Holy Name Cathedral
    Architectural Buildings, Sacred & Religious Sites
    See more photos
    RituandTim 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 Traveler
    • 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 #25 of 647 things to do in Chicago
    Certificate of Excellence 2014
    • Worth a peek inside, if you don't stay for the service 12/12/2018
    • Visited for Mass 12/09/2018
    • Holy Name Cathedral
    Address:
    735 North State Street
    Chicago, IL 60654-3835
    Phone:
    +1 312-787-8040
    Hours:
    Sun
    6:30 AM - 7:00 PM
    Mon - Fri
    5:30 AM - 7:00 PM
    Sat
    7:30 AM - 9:00 PM
    Other:
  • North Avenue Beach
    Beaches
    See more photos
    RituandTim 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 #56 of 647 things to do in Chicago
    • Nice Location 10/29/2018
    • Go to beach 10/22/2018
    • North Avenue Beach
    Address:
    1600 North Lake Shore Drive
    Chicago, IL 60613
    Phone:
    312 747 0832
    Hours:
    Sun - Sat
    10:00 AM - 3:00 PM
    Other:
  • Oak Street
    Points of Interest & Landmarks
    See more photos
    RituandTim 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 Traveler
    • 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 #100 of 647 things to do in Chicago
    • Quiet Now 09/16/2018
    • A nice stroll 09/13/2018
    • Oak Street
    Address:
    32 E Oak St # 200
    State St. to Michigan Ave.
    Chicago, IL 60611-1297
  • The Rookery Building
    Historic Sites, Architectural Buildings, Points of Interest & Landmarks
    See more photos
    RituandTim 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 #39 of 647 things to do in Chicago
    Certificate of Excellence 2014
    • Visually Appealing 12/11/2018
    • Frank Lloyd Wright creation 11/22/2018
    • The Rookery Building
    Address:
    209 S La Salle St
    Chicago, IL 60604-1219
    Phone:
    +1 312-994-4000
    Hours:
    Mon - Fri
    8:00 AM - 6:00 PM
    Sat
    8:00 AM - 2:00 PM
    Other:
  • Intelligentsia Coffee
    Restaurants (Cafe)
    RituandTim 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 #972 of 6,267 restaurants in Chicago
    • Great coffee, vibes, service 12/11/2018
    • Smooth coffee 10/06/2018
    • Intelligentsia Coffee
    Address:
    3123 N Broadway St
    Chicago, IL 60657-4522
    Phone:
    +1 773-348-8058
    Price range:
    $1 - $20
    Hours:
    Mon - Fri
    6:30 AM - 9:00 PM
    Sat - Sun
    7:00 AM - 9:00 PM
    Other:
  • The Magnificent Mile
    Neighborhoods, Points of Interest & Landmarks
    See more photos
    RituandTim 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 Traveler
    • 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 #4 of 647 things to do in Chicago
    Certificate of Excellence 2014
    • Magnificent! 12/12/2018
    • Great, free fun! 12/11/2018
    • The Magnificent Mile
    Address:
    North Michigan Avenue
    Chicago, IL 60611
    Phone:
    +1 312-409-5560
    Other:
  • Navy Pier
    Theme Parks, Piers & Boardwalks
    See more photos
    RituandTim 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 #19 of 647 things to do in Chicago
    Certificate of Excellence 2014
    • Much better in Chicago 12/12/2018
    • Lots to do 12/12/2018
    • Navy Pier
    Address:
    600 E Grand Ave
    Chicago, IL 60611-3419
    Phone:
    +1 312-595-7437
    Hours:
    Sun - Thu
    10:00 AM - 8:00 PM
    Fri - Sat
    10:00 AM - 10:00 PM
    Other:
  • The Art Institute of Chicago
    Art Museums
    See more photos
    RituandTim 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 647 things to do in Chicago
    Certificate of Excellence 2014
    • The World in a Building 12/12/2018
    • Well organized collection! 12/12/2018
    • The Art Institute of Chicago
    Address:
    111 S Michigan Ave
    159 East Monroe Street
    Chicago, IL 60603-6110
    Phone:
    +1 312-443-3600
    Price range:
    $25 - $25
    Hours:
    Thu
    10:30 AM - 8:00 PM
    Fri - Wed
    10:30 AM - 5:00 PM
    Other:
  • Millennium Park
    Parks, Points of Interest & Landmarks, Historic Walking Areas
    See more photos
    RituandTim 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 Traveler
    • 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 647 things to do in Chicago
    Certificate of Excellence 2014
    • Figure 8 Skate 12/12/2018
    • Very nice place 12/12/2018
    • Millennium Park
    Address:
    201 East Randolph Street
    Between Michigan Avenue & Columbus Avenue
    Chicago, IL 60601-6530
    Phone:
    +1 312-742-1168
    Hours:
    Sun - Sat
    6:00 AM - 11:00 PM
    Other:
  • 360 Chicago Observation Deck
    Points of Interest & Landmarks, Architectural Buildings, Observation Decks & Towers
    See more photos
    RituandTim 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 Traveler
    • Family
    Plan to stay:
    1-2 hours
    From the community
    Ranked #30 of 647 things to do in Chicago
    Certificate of Excellence 2014
    • Nice experience. I expected more from Tilt 12/10/2018
    • Nice view of chicago! 12/10/2018
    • 360 Chicago Observation Deck
    Address:
    875 N Michigan Avenue
    94th Floor
    Chicago, IL 60611-1803
    Phone:
    +1 312-751-3681
    Price range:
    $22 - $22
    Hours:
    Sun - Sat
    9:00 AM - 11:00 PM
    Other:
  • The Magnificent Mile
    Neighborhoods, Points of Interest & Landmarks
    See more photos
    RituandTim 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 Traveler
    • 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 #4 of 647 things to do in Chicago
    Certificate of Excellence 2014
    • Magnificent! 12/12/2018
    • Great, free fun! 12/11/2018
    • The Magnificent Mile
    Address:
    North Michigan Avenue
    Chicago, IL 60611
    Phone:
    +1 312-409-5560
    Other:
  • Shedd Aquarium
    Aquariums
    See more photos
    RituandTim Says:

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

    Good for
    • Must See
    • Thrifty Traveler
    • 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 #55 of 647 things to do in Chicago
    Certificate of Excellence 2014
    • Worth it 12/12/2018
    • Family time! 12/11/2018
    • Shedd Aquarium
    Address:
    1200 S. Lake Shore Drive
    Chicago, IL 60605-2490
    Phone:
    +1 312-939-2438
    Hours:
    Mon - Wed
    9:00 AM - 5:00 PM
    Thu
    9:00 AM - 3:00 PM
    Fri
    9:00 AM - 5:00 PM
    Sat - Sun
    9:00 AM - 6:00 PM
    Other:
  • Chicago Water Taxi
    Ferries, Taxis & Shuttles
    See more photos
    RituandTim 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 Traveler
    • 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 43 Transportation in Chicago
    Certificate of Excellence 2014
    • Take a ride on the Water Taxi! 11/25/2018
    • Loved the scenery and service 11/25/2018
    • Chicago Water Taxi
    Address:
    400 N Michigan Ave
    Chicago, IL 60611-4104
    Phone:
    +1 312-337-1446
    Hours:
    Sun - Sat
    6:45 AM - 9:00 PM
    Other:
  • Signature Lounge
    Jazz Clubs & Bars
    See more photos
    RituandTim 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 Traveler
    • Trendsetter
    • Solo
    • Friends
    • Couples
    • Senior
    • Family
    Tips
    • All year around...great spot!
    Plan to stay:
    2-3 hours
    From the community
    Ranked #15 of 581 Nightlife in Chicago
    Certificate of Excellence 2014
    • Weekend with friends and family 12/11/2018
    • Poor Customer Service 11/30/2018
    • Signature Lounge
    Address:
    875 N Michigan Ave
    John Hancock Center
    Chicago, IL 60611-1803
    Phone:
    +1 312-787-7230
    Hours:
    Sun - Thu
    11:00 AM - 12:30 AM
    Fri - Sat
    11:00 AM - 1:30 AM
    Other:
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