Chicago

Romantic Things to Do in Chicago - Valentine's Day & More

By Katie Sagal

Looking to plan a romantic getaway with your sweetheart? There are so many wonderfully romantic things to do in Chicago that it’s hard to choose our favorites. If you’re looking for romantic things to do in Chicago, either for Valentine's Day or for a romantic trip any time of year, check out a few of our top suggestions.

The Signature Lounge at Hancock Center

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Located atop the well-known John Hancock Center you'll find the romantic cocktail bar known as The Signature Lounge. The view from the 96th floor is phenomenal (to say the least), and the food and drink are equally exquisite. This is the perfect spot to wind down after a busy day or get geared up for a romantic evening out. Keep in mind that this venue is in high demand, and will both fill up quickly and come at a high price per drink. (I, for one, tend to limit myself to sipping a single drink slowly to enjoy the view.) If you'd like the take this evening to the next level -- literally -- a visit to 360 CHICAGO (just a bit lower on the tower) is a delightful addition to a romantic drink or two. You'll get to see the city skyline from above, including the shoreline of Lake Michigan and the easily identifiable Navy Pier Centennial wheel.

Skydeck Chicago (top of Willis Tower)

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Looking out from the Skydeck Chicago observation deck at the top of the Willis Tower (formerly Sears Tower) is one of the most romantic things to do in Chicago. You'll enjoy 360-degree views from the second tallest tower in the western hemisphere, taking your love to new heights in a serious way. For the most romantic view, head to the Skydeck at sunset or after dark when the city lights are glowing.

Explore the Art Institute of Chicago

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If you’re a fan of art, then there are few places as romantic, in Chicago, as the #1 rated museum in the country, the Art Institute of Chicago. They’ve got some of the best collections of Impressionist Art, some gorgeous Chagall stained glass windows, plus an impressive array of sculpture, textiles, antiquities and more. Check out their seasonal special exhibits for details on new and exciting things on display right now, or hit up their permanent collections for a few love-themed pieces like their collection of 19th century Valentines and sexy photographs.

Centennial Wheel at Navy Pier

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This 15-story Centennial Wheel is located at one of the most visited attractions in Chicago, at the exciting Navy Pier. Recently redesigned as part of their centennial project, the Centennial Wheel offers beautiful sights at thrilling heights. You can even enjoy free days once per month! From the top of the famous Centennial wheel, you and your partner will escape the crowd for a few minutes for some alone time with the scenic skyline and Lake Michigan views. After you disembark from the Centennial Wheel, Navy Pier is a lakeside wonderland to explore. You'll find romantic restaurants, shops, and other top-class attractions as you stroll along with your loved one. If you plan it right, you can even pick up tickets to a show at the well-regarded Shakespeare Theater, also located on the Pier.

Attend a Show

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Chicago’s theater scene is pretty unbeatable when it comes to variety and quality of performances. From the traditional (like you’d find at the Shakespeare Theater on Navy Pier) to the avant-garde, there’s something for all tastes. Because a theatrical performance is a pretty hot idea for Valentine’s Day, be sure to secure tickets in advance! You may be able to find discounted tickets by signing up for theater-specific mailing lists and websites like Goldstar.

Stroll the Beautiful Parks

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While Millennium Park is often the favorite for cultural activities and current events, Grant Park has just as much in the way of sightseeing and beautiful scenery. Or, check out the Lurie Garden to find the hidden beauty of wintertime plants. Whichever venue you choose, the real treasure is in the journey. If you’re planning a date in the warmer months, be sure to check out Buckingham Fountain, a truly impressive array of water jets set against the impressive Chicago skyline. Of course, if you're visiting during the winter months around Valentine's Day and can't bear the Chicago winter cold, then a visit to the Chicago Botanic Garden is another nice option. Stick with their indoor exhibits to see some lovely tropical plants and flowers.

Enjoy a Romantic Meal

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A romantic dinner is a classic for a reason. It’s hard to go wrong with a well-researched dinner venue this time of year, especially if they’re offering special Valentine’s Day meals or menus. It’s a great break from your own cooking and a good way to pry yourself away from Netflix. Downtown Chicago has tons of great restaurant options, many of which are in easy distance of several other great attractions to help you plan a larger itinerary. Remember to book your table early on a site like OpenTable to avoid last-minute panic!

Remember to Save on Attraction Admission

So there you have it. Our list of some romantic things to do in Chicago, just in time for Valentine's Day. Remember, some of these great options are included on the All-Inclusive Pass and the Explorer Pass from Go City, where you can save up to 55% on combined admission vs paying at the gate.

Katie Sagal
Go City Travel Expert

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A boat traveling along the Chicago River
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How to spend 5 days in Chicago

You’ve done the sensible thing and decided to spend 5 days in Chicago. Fantastic! The US ‘second city’ has a range of attractions that many other destinations simply can’t compete against – from magnificent art galleries to lake shore beaches. With a 5 day Chicago itinerary you’ll have the time you need to take in the city’s atmosphere alongside its landmark buildings. You’ll also be able to enjoy some of the city’s more off-beat things to see and do. For a round up of all that’s going on in Chicago, check out our favorite way of spending 5 days in the city. Day 1 – Downtown Chicago With your first hours in Chicago, it’s a good idea to get to grips with the downtown area – otherwise known as the Loop. The location of many of the city’s major landmarks, you’ll be spending much of your time here so it makes sense to get a feel of what’s located where. Whilst one of the most walkable cities in North America, you’re not going to want to wear out your shoe leather on day 1. Nor are you going to want to tackle Chicago’s public transportation, so instead head to one of the dozen stops included on the city’s Hop-on Hop-off sightseeing bus. The whole circular tour lasts for two hours and is accompanied by an audio narration providing a perfect introduction to the city. However, it’s unlikely you’re going to be able to avoid jumping off at a couple of points of interest. North Michigan Avenue – better known as the Magnificent Mile – is one of the city’s top places to be, blending suited office workers with luxury brands, much-loved restaurants, historic landmarks such as the Old Water Tower and views from 1000 feet up from the floor-to-ceiling windows of 360 CHICAGO in the John Hancock Center. Showing all that Chicago has to offer, it’s just a short stroll to the Museum of Contemporary Art – turn off on either East Pearson Street or East Chicago Avenue to get there for an afternoon amongst the greats of twentieth century art. Day 2 – Lake Michigan You will have already seen its vast expanse from 360 CHICAGO, but day 2 gives you the chance to explore the Lake Michigan shoreline. Start to the north of the Loop in Lincoln Park for views of western lowland gorillas and kangaroos at Lincoln Park Zoo. Then soak up the sun on North Avenue Beach (weather permitting). If you can tear yourself away from the beautiful setting, keep the shoreline to your left as you wander south back into the Loop by way of the upmarket Gold Coast neighborhood. On reaching Navy Pier, there are further options for taking in the Chicago skyline, by slipping into one of the gondolas of Centennial Wheel, which rise to a height of almost 200 feet. Swap gondolas and sidewalks for the lakeshore cycle track by picking up a bike at the pier’s Bike and Roll rentals. Ease yourself into the saddle by making the short journey to Chicago’s Museum Campus, incorporating the Field Museum, Shedd Aquarium and Adler Planetarium, either one of which will round off the afternoon hours with aplomb. Day 3 – Chicago from the water You’ve taken it in from high up and cycled along it, so there’s nothing more to do than get onto the water and explore Chicago from another angle, especially if your visit to the Shedd Aquarium gave you a feel for life in and on the waves yesterday. Unveiling hidden gems amongst the world-famous landmarks, taking a cruise along the three branches of the Chicago River is like slipping through the city’s two centuries of history. Its shift in architectural styles reveals itself as you cruise the calm blue waters beneath bridges and past structures including the giant art deco Merchandise Mart building and Willis Tower – for many years the tallest building in the world. Follow the river to its natural conclusion and you’ll find yourself floating on Lake Michigan. A Skyline Lake Tour does a similar job to river cruises, but arguably on an even greater scale. Departing from Navy Pier, tours take in the lakeshore forming the natural eastern boundary of the Loop, with commentary providing interesting tidbits of information, such as the fact Batman’s Gotham City is based on the skyscrapers of Chicago. But for an extra-special tour on the water don’t miss your chance to board Windy, Chicago’s official tall ship. With its sails filled with the wind the city is famous for, you’ll tack across Lake Michigan in a fashion almost entirely unchanged since the birth of steam. Day 4 – Chicago culture and more Keep up the pace of your Chicago in 5 days trip by starting day 4 with a few hours in another of the city’s top museums – the Museum of Science and Industry. A great choice for all the family, there are plenty of interactive exhibits, alongside flight simulators, important landmarks in transport and a gallery of exquisite model ships – should your trip aboard the Windy have gotten you hooked on all things nautical. Continue your exploration of Chicago’s culture by seeing a show. The Second City theater is well-known in comedy circles as the place to head for improv and the chance to catch the next big thing before the rest of the world. The Chicago Theater has a busy schedule of plays and pop concerts. Failing that, it’s also possible to head behind the scenes with a Chicago Theater Marquee Tour. Then enjoy a bite to eat. AT&T Plaza beneath the Cloud Gate sculpture in Millennium Park is home to an open-air restaurant during the warmer months of the year – replaced by one of the city’s top skating destinations during the winter. Day 5 – Get active End your 5 days in Chicago by mixing up the museum visits and river tours with some physical activity. Maggie Daley Park – immediately east of Millennium Park – has plenty of ways to do this, from free climbing walls and tennis courts to a skating ribbon from November to March. If you need a breather, there are shady groves for picnics in the sun, alongside one of the finest children’s playgrounds we’ve seen rising high above it all. One of Major League Baseball’s oldest arenas, Wrigley Field is a must-see for sports fans. Home of the Chicago Cubs, there’s no better way to understand the city psyche than attending a game. Alternatives include basketball from the Chicago Bulls and ice hockey from the Blackhawks both at the United Center. Save on admission in Chicago Sounds expensive? 5 days in Chicago doesn’t have to be! Go City lets you enter many of Chicago’s top attractions and landmarks with incredible savings versus advertised prices. It means you can do much more on your trip to Chicago than you thought you could without having to worry about your bank balance once!
Ian Packham
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Best Chicago Souvenirs

Taking a trip to Chicago soon? It’s likely you’ll want to take something back home with you that reminds you of your trip. It’s equally likely you’ll want to buy a small item for friends and family you left behind. If you want to find souvenirs made in Chicago rather than tacky plastic items that have no real link with the city, you’ve come to the right place. We’ve got some fantastic ideas for the best Chicago souvenirs below! Edible Chicago souvenirs The main problem with edible gifts from the windy city is having the willpower to avoid consuming them all before you’ve even left downtown. Don’t be put off by the long lines which often stretch down the street from the Garrett Popcorn shops on West Jackson Boulevard and Michigan Avenue. Dishing up their ‘Chicago Mix’, half cheese and half caramel, to the people of the city since 1949, they’re clearly doing something right. Small bags cost as little as $3, though the souvenir skyline tins make a great keepsake long after the popcorn itself is all gone. They also have outlets at O’Hare Airport. With a pedigree dating back even further is Fannie Mae chocolates, which have been Chicago based since first opening in 1920. Head to one of their city center stores and you’ve got the option of creating your own mix of pixies, mint meltaways and vanilla buttercreams. At the upper end of the chocolate market is the Chicago-only Vosges Haut-Chocolat. With each chocolate hand-finished, the company is particularly well-known for their truffles, with flavors as diverse as hazelnut and balsamic vinegar and ginger with wasabi. As some indication of price, a box of 16 truffles will set you back around $50. On the savory front, The Spice House on North Wells Street in the Lincoln Park neighborhood (close to Chicago History Museum) offers more than the usual cooking herbs and spices. Their team has created a range of Chicago-themed blends that will brighten up your home cooking for weeks to come. Drinkable Chicago souvenirs The same can be said for another much-loved Wells Street store, Old Town Oil. Specializing in small-batch olive oils and vinegars from farms across the globe, they have some very tasty-looking gift boxes, and can even produce custom bottle labels. Oils and vinegars won’t quench your thirst, but beers will, with Goose Island an award-winning craft brewery set up to bring good beers to the Chicago streets. Using 15 different yeasts to turn the sugars into alcohol before aging the beer in bourbon barrels for extra flavor, visitors are welcome to the brewery tap room on Fulton Street or its Clybourn brewhouse to sample their selection of seasonal and year-round beers. With over 100 international prizes to its name, the Koval Distillery has come a hell of a long way since starting up in 2008 as the first new distillery in the city since the 1800s. Their copper vats produce whiskeys, gins and specialty spirits using organic grains. Everything from soaking of the grain to bottling takes place in house so the dedicated team are able to keep track of every step to produce their signature clean flavors. Jewelry and curios The Field Museum is another great place to keep a lookout for souvenirs. Its store is awash with goodies, though we’ve chosen to focus our attention on their jewelry selection. Linking back to the museum’s incredible natural history collection, it ranges from T-Rex earrings to necklaces and pendants threaded with natural stones such as quartz and onyx. Echoing the form of Chicago’s favorite piece of public art – Anish Kapoor’s Cloud Gate – Tiffany & Co’s Chicago store sells sterling silver bean pendants designed by Elsa Peretti. If the price tag stops you stepping beyond the window displays, various other outlets do similar pieces in base metals. But if it’s a wall in your house you’re thinking of decorating, the store at the Museum of Contemporary Art has a variety of art-based items, from $10 fridge magnets to mobiles based on Bauhaus and surrealist principles which would provide a dash of color to any room. Wearable Chicago souvenirs A sports mad city with professional basketball, ice hockey, baseball and American football teams, getting tickets to a game is an unmissable Chicago experience. And to remember it, what could be better than your very own jersey? Each stadium and arena have their own store, but you can also find items linked to all Chicago’s teams at stores including Clark Street Sports. So whether it’s an oversized foam finger or an official wristband emblazoned with the Chicago Cubs logo, odds are you’ll find it here. Thanks to an array of nationwide and boutique local stores, fashionistas can also take something home that will forever remind them of their time in the windy city. Independent Wolfbait & B-Girls is a marketplace offering the wares of 250 local artisans, including clothing you won’t find anywhere else and an almost endless pick of potential gifts. Other quirky establishments include Optimo Fine Hats, offering custom headgear for men whatever the occasion. Grabbing a T-shirt with the Chicago skyline will help your little ones remember their trip to Chicago, or make them want to visit themselves one day if they weren’t with you. Other items linked to the city’s architecture include ever-popular snow globes containing representations of the Willis Tower and Skydeck amongst other landmark buildings. Spend on the things that count with the best Chicago souvenirs The best Chicago souvenirs are those which continuously remind you of all the good times you had at the city’s attractions. That good time will be made all the better if you’ve visited them with Go City. Explore the city in this way and you’ll be able to take advantage of substantial savings on entrance admission to many of the top attractions and things to do. So why not check out our pass options and join the thousands of visitors who have already done just this?
Ian Packham
Skydeck Chicago Skyline
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Visiting SkyDeck Chicago at Willis Tower

Take a trip to the top of the Willis Tower - daredevils will love The Ledge, while foodies will be thrilled with the Pie in the Sky experience.
Katie Sagal

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