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Romantic Guide to Chicago

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Chicago's location along the waters of Lake Michigan gives it an automatic head start for romance. The Windy City offers couples everything they need to celebrate their affections in a picturesque, diverse, and energetic environment: Historic landmarks, trendy restaurants, iconic skyscrapers and a vibrant city buzz represent the landscape that is Chicago.

Good for
  • Couples
  • Trendsetter

6 Places

6 City Tips

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Map

6 Places

Buckingham Fountain

Fountains, Points of Interest & Landmarks

Lakefront Trail

Biking Trails, Hiking Trails

Lyric Opera of Chicago

Operas

Giordano's Pizza

Restaurants

Skydeck Chicago - Willis Tower

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

Alinea

Restaurants

TawannaCB's City Tips

  • Chicago has a well developed transportation system. Getting around is quick and inexpensive. Consider a one-day visitors pass for unlimited bus and train rides.
  • You can catch a cab from just about anywhere in the city.
  • Chicago is called the Windy City for a reason. You'll want to carry an extra layer or so during fall and winter months.
  • The most popular attractions are downtown and within walking distance of each other.
  • Restaurants in downtown Chicago can be expensive — look to other neighborhoods if on a budget.
  • Tipping is typically 15% or more of the bill.
  • Save
    Buckingham Fountain
    Fountains, Points of Interest & Landmarks
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    TawannaCB Says:

    Buckingham Fountain is impressive in size yet still maintains artistic beauty. Located in the heart of the city, it’s a popular spot for locals and visitors alike, with the backdrop of the lake and several other attractions promising a good view. Its timed water displays, complete with lights, are a particularly romantic crowd-pleaser.

    Good for
    • Must See
    • Art and Architecture Lover
    • Like a Local
    Tips
    • After sunset from spring to fall, there’s a water and light show every twenty minutes at the fountain.
    • During the winter months, the fountain’s water is turned off.
    Plan to stay:/
    Less than 1 hour
    From the community
    Ranked #22 of 659 things to do in Chicago
    Certificate of Excellence 2014
    • Nice Area to Visit 15/10/2017
    • Lovely and romantic 14/10/2017
    • Buckingham Fountain
    Address:
    Grant Park
    Chicago, IL
    Phone:
    +1 312-742-7529
    Hours:
    Sun - Sat
    08:00 - 23:00
    Other:
  • Save
    Lakefront Trail
    Biking Trails, Hiking Trails
    See more photos
    TawannaCB Says:

    The Lakefront Trail is one of the best locations in the city to take in Chicago’s picturesque skyline and architecture. Runners, bikers, and walkers populate the trail in search of fitness or just a leisurely time outdoors. Enjoy fireworks displays as you cruise along the lakefront by boat, or simply stroll along the trail, arm in arm.

    Good for
    • Peace and Quiet Seeker
    • Must See
    • Nature Lover
    Tips
    • Rent a bike and take time to explore your surroundings.
    • Wear comfortable shoes on the trail and be sure to watch your step in some areas.
    Plan to stay:/
    2-3 hours
    From the community
    Ranked #11 of 659 things to do in Chicago
    Certificate of Excellence 2014
    • Great Way to View the City 16/10/2017
    • Great Relaxing Walk 15/10/2017
    • Lakefront Trail
    Address:
    540 N Lake Shore Dr
    Chicago, IL 60611-3414
    Phone:
    +1 312-742-7529
    Other:
  • Save
    Lyric Opera of Chicago
    Operas
    See more photos
    TawannaCB Says:

    The opera bellows romance and this is an amazing venue in which to enjoy it. The Lyric Opera House is a stunningly beautiful piece of architecture with pitch perfect acoustics, and its classical atmosphere is a real city treasure, made to be shared.

    Good for
    • Must See
    • Luxury Traveller
    • Like a Local
    • Friends
    • Couples
    • Senior
    • Art and Architecture Lover
    • Nightlife Seeker
    Tips
    • The theater is very large; consider bringing small binoculars if you wish to see the performers' faces up close.
    Plan to stay:/
    2-3 hours
    From the community
    Ranked #58 of 659 things to do in Chicago
    Certificate of Excellence 2014
    • Very nice place, and the show of My Fair Lady was perfect. 29/05/2017
    • It's incredible visit of the lyric opera 28/05/2017
    • Lyric Opera of Chicago
    Address:
    20 N Wacker Dr
    Chicago, IL 60606-2806
    Phone:
    +1 312-827-5600
    Other:
  • Save
    Giordano's Pizza
    Restaurants (Italian, Pizza)
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    TawannaCB Says:

    Arguably the best restaurant in Chicago for deep dish pizza, Giordano’s has been serving its delicious version of this local favorite for 40 years. The crust on the deep dish pizzas are flaky, buttery and absolutely perfect for sharing.

    Good for
    • Foodie
    • Must See
    Tips
    • The pizza is substantial. If you're ordering an appetizer, opt for something on the lighter side.
    Plan to stay:/
    1-2 hours
    From the community
    Ranked #99 of 5,959 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
    Skydeck Chicago - Willis Tower
    Architectural Buildings, Observation Decks & Towers, Points of Interest & Landmarks
    See more photos
    TawannaCB Says:

    For a 360 degree panoramic view of Chicago, carve out some time to visit Skydeck. A movie prior to your journey will educate you on the history of Chicago, before you're promptly whisked up 103 floors to the top of the Willis Tower — enough to sweep anyone off their feet!

    Good for
    • Must See
    • Like a Local
    • Solo
    • Friends
    • Couples
    • Thrill Seeker
    • Family
    • Nature Lover
    Tips
    • Be prepared to wait for up to an hour: everybody wants to go to the top!
    • The Willis Tower was formerly known as the Sears Tower.
    Plan to stay:/
    1-2 hours
    From the community
    Ranked #15 of 659 things to do in Chicago
    Certificate of Excellence 2014
    • Old Sears Tower 16/10/2017
    • 0% visibility kind of day :-/ 15/10/2017
    • Skydeck Chicago - Willis Tower
    Address:
    233 S. Wacker Drive
    Entrance on Jackson Blvd
    Chicago, IL 60606-7147
    Phone:
    +1 312-875-9447
    Price range:
    US$22 - US$22
    Hours:
    Sun - Sat
    09:00 - 22:00
    Other:
  • Save
    Alinea
    Restaurants (American, International)
    See more photos
    TawannaCB Says:

    For a fine dining experience that you'll always remember, dine at Alinea's. Although you'll pay a premium to dine here, it's an experience not to be missed. Dishes are plated beautifully and the chef takes you on a journey of new discoveries through his many unique menu offerings.

    Good for
    • Foodie
    • Couples
    • Luxury Traveller
    • Trendsetter
    Tips
    • Alinea has a long waitlist for reservations. Book at least 2 months in advance.
    Plan to stay:/
    2-3 hours
    From the community
    Ranked #2 of 5,959 restaurants in Chicago
    Certificate of Excellence 2014
    • AmaIng beyond words 14/10/2017
    • Wine Pairing Was Average 02/10/2017
    • Alinea
    Address:
    1723 North Halsted St
    Chicago, IL 60614-5501
    Phone:
    +1 312-867-0110
    Price range:
    US$150 - US$1,000
    Hours:
    Wed - Sun
    17:00 - 21:00
    Other:
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