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Only have three days to spend in Chicago? Here are some of my favorite places that can be squeezed into a short amount of time in the city.

Good for
  • Shopping Fanatic
  • Nightlife Seeker
  • Nature Lover

12 Places

3 City Tips

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12 Places

Day 1

Chicago Riverwalk

Historic walking areas

Millennium Park

Parks, Landmarks & points of interest, Historic walking areas

Art Institute of Chicago

Art museums

Gino's East

Restaurants

Howl at the moon

Restaurants

Day 2

The Magnificent Mile

Neighbourhoods, Landmarks & points of interest

Water Tower Place

Malls

360 Chicago

Observation decks & towers, Architectural buildings

Second City

Comedy clubs

Day 3

Shedd Aquarium

Aquariums

Buckingham Fountain

Fountains, Landmarks & points of interest

Rock Bottom Restaurant & Brewery

Restaurants

Diana R's City Tips

  • The Chicago CTA offers unlimited 3 day passes on public transit. Why not grab one to move freely around the city for less?
  • Chicago is famous for its deep dish pizza, so if you're going to give it a try, remember that it'll take at least 45 minutes to cook after you order. It's delicious!
  • The weather can be extreme in Chicago, so if it's summer it'll be very hot, and if it's winter, pack for freezing temperatures.
    Day 1
  • Save
    Chicago Riverwalk
    Historic walking areas
    See more photos
    Diana R Says:

    The best way to start your trip in Chicago is with a tour down the river, learning about the history and architecture of the buildings. If the weather's nice, there's no better way to be introduced to the city! Another option is to just walk along the river and take in the grandeur of the skyscrapers along its edge — many excellent photo opportunities!

    Good for
    • History Buff
    • Nature Lover
    Tips
    • If you go for the tour, remember to double check availability, as it operates seasonally.
    Plan to stay:
    1-2 hours
    From the community
    Ranked #34 of 252 attractions in Chicago
    • Nice walk, though at times a little treacherous in winter 20/11/2014
    • Great city view 06/11/2014
    • Chicago Riverwalk
    Address:
    100 E. Wacker Drive
    Chicago, IL
  • Save
    Millennium Park
    Parks, Landmarks & points of interest, Historic walking areas
    See more photos
    Diana R Says:

    A trip to Chicago wouldn't be complete without a photo of your reflexion in 'the bean.' Head on over to Millennium park to pose with friends with a warped Chicago skyline in the background. Some of the best photos include the skyline at night, but any time of day will give you great shots!

    Good for
    • Must See
    • Art and Architecture Lover
    • Nature Lover
    Tips
    • The bean can be quite crowded, so before you run up to it, make sure you're not interrupting someone else's photo!
    Plan to stay:
    1-2 hours
    From the community
    Ranked #4 of 252 attractions in Chicago
    Certificate of Excellence 2014Certificate of Excellence 2014
    • Valentines Weekend 26/02/2015
    • Outdoor Fun! 26/02/2015
    • Millennium Park
    Address:
    201 E Randolph St
    Between Michigan Ave. & Columbus Ave.
    Chicago, IL 60602
    Phone:
    312-742-2963
    Hours:
    Sun - Sat
    6:00 - 12:00
    Other:
  • Save
    Art Institute of Chicago
    Art museums
    See more photos
    Diana R Says:

    Whenever I have friends in town, I always send them to the Art Institute because it's so much fun to explore. This fantastic art museum is open from 10.30am until 5pm, with a late night on Thursdays until 8pm. Group and self-guided tours are also available if you feel so inclined.

    Good for
    • Must See
    • Like a Local
    • Art and Architecture Lover
    Tips
    • Free entry every Thursday, 5pm - 8pm.
    Plan to stay:
    More than 3 hours
    From the community
    Ranked #1 of 252 attractions in Chicago
    Certificate of Excellence 2014Certificate of Excellence 2014
    • Outstanding 26/02/2015
    • Not to be missed! 26/02/2015
    • Art Institute of Chicago
    Address:
    111 S Michigan Ave
    Chicago, IL 60603-6404
    Phone:
    312 443 3600
    Hours:
    Thu
    10:30 - 9:00
    Fri - Wed
    10:30 - 6:00
    Other:
  • Save
    Gino's East
    Restaurants (Pizza)
    See more photos
    Diana R Says:

    After a day outdoors you'll have worked up a big appetite. Head on over to Gino's East for a famous Chicago-style deep dish pizza. Gino's East is one of the best pizza places in Chicago — and believe me, I've tried them all.

    Good for
    • Foodie
    • Like a Local
    Tips
    • Remember to pace yourself! If you haven't had this type of pizza before, it can be very filling so be sure to take some time between slices to avoid becoming uncomfortably full.
    • Go early to avoid the dinner rush — your pizza will take about 45 minutes to cook, so even if you're seated right away, you'll be hungry by the time it arrives.
    Plan to stay:
    1-2 hours
    From the community
    Ranked #562 of 4,352 restaurants in Chicago
    • Great Pizza 23/02/2015
    • Best Pizza 20/02/2015
    • Gino's East
    Address:
    500 N. LaSalle St
    Chicago, IL 60654
    Price range:
    $0 - $30
    Hours:
    Sun - Thu
    11:00 - 11:00
    Fri - Sat
    11:00 - 12:00
    Other:
  • Save
    Howl at the moon
    Restaurants (American, Bar, Brew Pub)
    See more photos
    Diana R Says:

    If you still have energy left after a long day exploring, head on over to this dueling piano bar and sing the night away! Put in your requests for songs, or pay the pianist to stop the ones you don't like. It's guaranteed fun for everyone.

    Good for
    • Friends
    • Couples
    • Art and Architecture Lover
    • Nightlife Seeker
    Tips
    • If you arrive early enough there isn't a cover charge to get in.
    Plan to stay:
    2-3 hours
    From the community
    Ranked #331 of 4,352 restaurants in Chicago
    Certificate of Excellence 2014Certificate of Excellence 2014
    • Great place for early or late drinks and fun entertainment 25/02/2015
    • great night 20/02/2015
    • Howl at the moon
    Address:
    26 W Hubbard St
    Chicago, IL 60610
    Phone:
    (312) 863-7427
    Hours:
    Sun
    19:00 - 15:00
    Mon - Fri
    17:00 - 15:00
    Sat
    17:00 - 16:00
    Other:
  • Day 2
  • Save
    The Magnificent Mile
    Neighbourhoods, Landmarks & points of interest
    See more photos
    Diana R Says:

    Even if you don't like to shop, you can't visit Chicago without at least taking a stroll down a couple of blocks of this famous strip. If your favorite store is usually difficult to find, odds are they do have an outpost in Chicago!

    Good for
    • Must See
    • Luxury Traveller
    • Trendsetter
    • Shopping Fanatic
    Tips
    • There are plenty of stores just off the Magnificent Mile as well — Rush Street, for example, runs parallel, and also has 5-star restaurants in case you get hungry.
    Plan to stay:
    More than 3 hours
    From the community
    Ranked #32 of 252 attractions in Chicago
    • Great Shopping, Great Food! 22/02/2015
    • Indispensable on every trip 21/02/2015
    • The Magnificent Mile
    Address:
    N Michigan Ave
    Chicago, IL 60611
    Phone:
    312 642 3570
  • Save
    Water Tower Place
    Malls
    See more photos
    Diana R Says:

    Located on the Magnificent Mile, this shopping center gives your wallet a break from all of the luxury shops lining the street. It's worth stopping by to appreciate the architecture and find your other favorites that aren't so exclusive.

    Good for
    • Must See
    • Shopping Fanatic
    Tips
    • Water Tower is located right by 360 Chicago, so it's easy to check them both out while at this end of town.
    Plan to stay:
    2-3 hours
    From the community
    Ranked #5 of 160 shopping & fashion in Chicago
    • A girls dream - 7 floors of shopping! 26/02/2015
    • Respite from Lake Michigan winds 24/02/2015
    • Water Tower Place
    Address:
    835 N. Michigan Avenue
    Chicago, IL 60611
    Phone:
    (312) 440-3166
    Hours:
    Sun
    10:00 - 7:00
    Mon - Sat
    10:00 - 10:00
    Other:
  • Save
    360 Chicago
    Observation decks & towers, Architectural buildings
    See more photos
    Diana R Says:

    If you haven't seen Chicago from above, 360 Chicago is for you! Formally called the John Hancock observatory, 360 Chicago can be accessed from the north end of the Magnificent Mile. You can buy a ticket for one visit, or for a morning plus night visit to see how the skyline changes when looking at it from 94 floors up!

    Good for
    • Must See
    • Luxury Traveller
    • Like a Local
    Tips
    • If your budget allows, skip the observation floor and head up to the Signature room on the 95th floor for a fancy lunch or dinner instead. Or grab a drink in the Signature Lounge!
    Plan to stay:
    1-2 hours
    From the community
    Ranked #12 of 252 attractions in Chicago
    Certificate of Excellence 2014Certificate of Excellence 2014
    • Try the new TILT experience! 27/02/2015
    • By far the best! 25/02/2015
    • 360 Chicago
    Address:
    875 N Michigan Ave
    94th Floor
    Chicago, IL 60611
    Phone:
    +1 312-751-3681
    Hours:
    Sun - Sat
    9:00 - 12:00
    Other:
  • Save
    Second City
    Comedy clubs
    See more photos
    Diana R Says:

    One of my favorite ways to make my sides hurt: A night of laughing at the improv comedy at Second City! Snacks and alcohol are available throughout the performances, so that being said, this one is not for those traveling with kids.

    Good for
    • Like a Local
    • Trendsetter
    • Friends
    • Solo
    • Couples
    • Art and Architecture Lover
    • Nightlife Seeker
    Tips
    • The closest 'L' stop is Sedgwick, which can be accessed from the brown and purple line. From there it's just a few short blocks' walk away.
    • Check their schedule — shows usually start at 8pm and 11pm.
    Plan to stay:
    2-3 hours
    From the community
    Ranked #46 of 395 activities in Chicago
    Certificate of Excellence 2014Certificate of Excellence 2014
    • Great night! 26/02/2015
    • Comedy fun 24/02/2015
    • Second City
    Address:
    1616 N Wells St
    Chicago, IL 60614
    Phone:
    312-664-4032
    Other:
  • Day 3
  • Save
    Shedd Aquarium
    Aquariums
    See more photos
    Diana R Says:

    One of the best aquariums in the world and open rain or shine — don't leave Chicago without spending the day exploring! You can see Nemo, sharks, seals and more, plus there are usually shows a few times throughout the day.

    Good for
    • Must See
    • Like a Local
    • Thrill Seeker
    Tips
    • Get there early — there's so much to see that you might not fit it all in one day!
    Plan to stay:
    More than 3 hours
    From the community
    Ranked #37 of 252 attractions in Chicago
    Certificate of Excellence 2014Certificate of Excellence 2014
    • Good, but not great. 24/02/2015
    • Variety! 22/02/2015
    • Shedd Aquarium
    Address:
    1200 S. Lake Shore Drive
    Chicago, IL 60605
    Phone:
    +1 312-939-2438
    Hours:
    Mon - Fri
    9:00 - 6:00
    Sat - Sun
    9:00 - 7:00
    Other:
  • Save
    Buckingham Fountain
    Fountains, Landmarks & points of interest
    See more photos
    Diana R Says:

    Visit the fountain at any point in your trip, but if you turn up at dusk there's a twenty minute water show with music and lights for you to enjoy!

    Good for
    • Must See
    • Art and Architecture Lover
    • Nature Lover
    Tips
    • Many couples take wedding photos in front of the fountain — go on a weekend and you might be able to see a beautiful bride as well!
    Plan to stay:
    Less than 1 hour
    From the community
    Ranked #15 of 252 attractions in Chicago
    Certificate of Excellence 2014Certificate of Excellence 2014
    • A great place to send the evening 27/02/2015
    • This gem is a calming oasis in Grant Park 21/02/2015
    • Buckingham Fountain
    Address:
    Grant Park
    Chicago, IL
    Hours:
    Sun - Sat
    8:00 - 12:00
  • Save
    Rock Bottom Restaurant & Brewery
    Restaurants (American)
    See more photos
    Diana R Says:

    Grab dinner or a few drinks at Rock Bottom Restaurant & Brewery. The portion sizes are large and the beer is delicious, so you might end up spending the whole night there if you're not careful!

    Good for
    • Foodie
    • Friends
    • Solo
    • Couples
    • Nightlife Seeker
    Tips
    • Rock Bottom can get busy, but they have plenty of beers to offer you while you wait — show up anytime for a dinner and/or drinks.
    Plan to stay:
    2-3 hours
    From the community
    Ranked #470 of 4,352 restaurants in Chicago
    Certificate of Excellence 2014Certificate of Excellence 2014
    • Wow what a surprise!!! 25/02/2015
    • Love Brew Pubs - this one had good beer 24/02/2015
    • Rock Bottom Restaurant & Brewery
    Address:
    1 W Grand Ave
    Chicago, IL 60654-4806
    Phone:
    312-755-9339
    Price range:
    $7 - $25
    Hours:
    Sun - Sat
    11:00 - 15:00
    Other:
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