Chicago
Valentine's Day

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Our most recommended Chicago Valentine's Day

360 Chicago: Observation Deck Entry with a Drink at Bar 94

1. 360 Chicago: Observation Deck Entry with a Drink at Bar 94

Take your cocktail hour to a whole different level at Bar 94, 360 Chicago's own inviting bar located 1,000 feet over Chicago’s spectacular Magnificent Mile. Part observation deck, part cocktail and beer destination, Bar 94 combines breathtaking views and taste-tempting cocktail combinations. Featuring locally crafted beers from Revolution Brewing and locally inspired spirits from KOVAL Distillery, Bar 94 combines amazing 360-degree views with premium beer, wine, and spirits to give you a taste of Chicago you can’t find anywhere else. Your admission includes access to 360 Chicago, formerly The John Hancock Observatory, which combines superior lake views with close-ups of Chicago’s monumental landmarks. With views consistently rated as Chicago’s best, no other tower gets you closer to the heart of Chicago. Located on the Magnificent Mile and close to Navy Pier, 360 Chicago also provides easy access to Chicago’s premier shopping and dining districts. Choose from a select drink menu as follows: • Cocktails: Tequila Sunrise: house tequila, orange juice, grenadine, served with a cherry Appleseed: house apple whiskey, lemonade, cranberry juice, a splash of soda, served with a cherry Vodka Spritzer: house citrus vodka, sour mix, soda water, and a splash of cranberry juice, served with a lemon Summer Punch: Rumhaven coconut rum, cranberry juice, orange juice, served with an orange Team Captain: Captain Morgan white rum, orange juice, Sierra Mist, served with a lime • Wine: White (Chardonnay), red (Cabernet Sauvignon), or rosé • Beer: Revolution Cross of Gold, Miller Lite, Miller High Life, Miller Genuine Draft

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Chicago: 45-Minute Private Helicopter Flight for 1-3 People

2. Chicago: 45-Minute Private Helicopter Flight for 1-3 People

Enjoy spectacular views of Chicago from an MD500 helicopter. This 45-minute helicopter flight over Chicago covers all the important highlights of the city from McCormick Place and Soldiers Field in the South to Wrigley Field in the North. Depart from Schaumburg Regional Airport and see some of Chicago's highlights including the Willis Tower, the John Hancock Building, Navy Pier, and Lake Michigan with its beaches and picturesque shoreline. Also see the Chicago River, Grant Park, Millennium Park, Buckingham Fountain, and Museum Campus. Make sure you also look out for Wrigley Field, home to the Chicago Cubs, and the United Center, where the Chicago Bulls and Blackhawks both play. This is a private helicopter experience for 1 to 3 passengers. Travel in complete safety with a professional pilot who will provide you with live commentary through noise-canceling headphones. In the summertime, have the added thrill of the doors being able to be off during the flight.

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Chicago: 1.5-Hour Romantic Sunset Cruise

3. Chicago: 1.5-Hour Romantic Sunset Cruise

Start your sunset cruise on the Chicago River at Michigan Avenue. Make your way along the main branch of the river towards Lake Michigan before entering the Chicago Locks, a modern engineering marvel, that will transfer the vessel onto the great Lake Michigan. The vessel will cruise along Lake Michigan as the sun sets behind the wonderful skyline offering several amazing views. Your local tour guide will give a very brief commentary along the Chicago River and entrance to Lake Michigan, but most of the 1.5-hour cruise is spent without narration, leaving you to watch the sun put on a beautiful display with the City skyline. Admire the many angles of the Chicago skyline from Lake Michigan, one of the largest bodies of fresh water in the world. Capture magical views of Chicago's twin super-skyscrapers, the famous Willis (formerly Sears) Tower and the John Hancock Building. You'll also get to admire the majesty of Grant Park with its famous Buckingham Fountain, and iconic Chicago venues such as Soldier’s Field, Adler Planetarium, and the Shedd Aquarium. During your cruise, treat yourself at the full-service cash bar featuring authentic Chicago products. Try local beer and spirits and Garrett’s Popcorn. Choose between the fresh air of the open-air decks or enjoy the comfort of the climate-controlled interiors during your cruise. Don’t forget to take a selfie at the Grand Staircase at the front of the boat or pose for photos at the picturesque stern or bow of this classic vessel.

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Chicago: 1.5-Hour Lake and River Architecture Cruise

4. Chicago: 1.5-Hour Lake and River Architecture Cruise

Experience an architecture cruise along the Chicago River and Lake Michigan, a family tradition since 1935. Admire Chicago’s historic and ever-changing skyline with a local expert guide as you cruise through the city. Choose between the open-air decks or the comfort of the climate-controlled interiors during the cruise. Start the cruise at Michigan Avenue (DuSable) bridge and go up the main branch of the Chicago River to Wolf Point before heading back past the Chicago Riverwalk towards Lake Michigan. Learn about historic skyscrapers like the Wrigley Building and the Tribune Tower, the deco Merchandise Mart, mid-century skyscrapers like the Mies Van der Rohe AMA Building, the circular Marina City Towers, the AON Center, and modernist structures like Aqua, Trump Tower, Nuveen, and the Vista Tower. After passing through the Chicago Lock and cruising past Navy Pier, admire the Chicago skyline from Lake Michigan, one of the largest bodies of fresh water in the world. Here you can also see the twin super-skyscrapers, the famous Willis (formerly Sears) Tower, and the John Hancock Building. See the majesty of Grant Park with its famous Buckingham Fountain, and iconic Chicago venues such as Soldier’s Field, Adler Planetarium, and the Shedd Aquarium. Enjoy several vantage points for memorable pictures throughout, and finally arrive back at Du Sable Bridge on Michigan Avenue.

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Chicago Seadog Speedboat Fireworks Cruise on Lake Michigan

5. Chicago Seadog Speedboat Fireworks Cruise on Lake Michigan

Enjoy a summer or autumn evening on this Chicago Seadog Speedboat Fireworks Cruise on Lake Michigan. This popular 60-minute narrated tour ensures you have the best views of this magnificent fireworks display. Every seat on the Seadog Speedboat Fireworks Cruise has amazing panoramic views of Chicago's historical skyline. Whether you are looking for a romantic evening, a night out with friends, or simply appreciate the art of pyrotechnics, this tour will have everyone of all ages leaving with a smile. Come and visit all of the possibilities that Chicago has to offer by enjoying a magical Fireworks Cruise on Lake Michigan. These memories are made to last a lifetime!

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Chicago: Photo Shoot with a Private Vacation Photographer

6. Chicago: Photo Shoot with a Private Vacation Photographer

The tour provider will organize the locations for your photo shoot based on your own unique requirements, whether it be a family getaway, a romantic trip or a livelier one with friends.  Once the details are organized, you will receive confirmation of all the information you need, leaving you to simply meet the photographer on location in Chicago on the day and let them work their magic, capturing your travels in a contemporary and candid style of photography. Your Chicago vacation photographers are handpicked and highly experienced in addition to being local experts and will share their knowledge of the city with you like an old friend. Once your photo tour has finished, you will receive a link to your own personal online gallery (password protected) within 5 working days, containing your professionally edited images, all free to download. This photo tour will allow you to look back over your travels with fond memories, when all too often you are left with rusty memories of your journeys. Make sure that the next time you travel, you will have mementoes that will last a lifetime and beyond.

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Other Sightseeing Options in Chicago

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What people are saying about Chicago

Absolutely fantastic boat excursion on the Chicago River! Very nice boat with a great crew eager to please! Bar service was excellent and the narration of the buildings and surrounding area was so informative. The guide also added local historical facts to the narration which was a great added bonus. I would highly recommend this cruise and this company for your Chicago River experience!

Beautiful views, the architecture is amazing and the guide never left is with a dull moment. he was amazingly knowledgeable about everything we saw, and some things we didn't--much history!

Die Tour ist zu 100% empfehlenswert. Besonders bei gutem Wetter wunderschön! Unser Guide "Dave" war der Beste guide den ich jemals auf einer Tour hatte.

Was my first time in Chicago and to have the oportunity of seeing the city in other way is amazing.

Awesome experience and the drinks were great!! Bartenders were so friendly too!! Would go again!!