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ChicagoActivities for couples

Our most recommended Chicago Activities for couples

Chicago: 360 Chicago Observation Deck Skip-the-Line Ticket

1. Chicago: 360 Chicago Observation Deck Skip-the-Line Ticket

Marvel at the views from 1,000 feet over Chicago’s legendary Michigan Avenue with this ticket to the 360 CHICAGO observation deck on the 94th floor of the John Hancock Center. Save time with skip-the-line access to this popular attraction. Head up to the 360 CHICAGO observation deck to take in breathtaking views of Chicago’s lakefront and view the city skyline from above. Take a peek at 4 neighboring states from this height. Feel the thrill of a 40-second ride in one of North America's fastest elevators to the observation deck to experience what 'Travel & Leisure Magazine' voted one of the best views in America. Enjoy an interactive exhibit on the Ground Floor that highlights Chicago’s rich history and showcases 9 of the city’s culturally unique neighborhoods. On the 94th floor, explore the history and architecture of the magnificent city stretched out before you. To enhance your experience, download the Magnicity App for a guided tour right from your smartphone. The App includes an interactive viewfinder, unique facts, stories and recommendations. Enjoy a thrilling photo opportunity at CloudWalk, a breathtaking 3D mural with the optical illusion of walking in the clouds. Relax and take in the view at the 94th floor’s Cloud Bar which serves up iconic Chicago snacks, neighborhood-inspired Cocktails, and a local brew, Moody Tongue, on tap. By purchasing this timed ticket, you get to skip the ticket desk and present your barcoded voucher to security to be scanned - you may have to wait in a short line at security, then head directly into the Ground Floor Exhibits, and then on to the Elevator Line.

Chicago: 1.5-Hour Lake and River Architecture Cruise

2. 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.

Chicago: 1.5-Hour Romantic Sunset Cruise

3. Chicago: 1.5-Hour Romantic Sunset Cruise

Relax as you glide over the Chicago River and into Lake Michigan on this cruise. Enjoy the glow of the sunset on Chicago's sparkling skyline. Have the option to purchase delectable drinks and snacks at the onboard bar as you sail. 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.

Chicago: Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise

4. Chicago: Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise

Discover Chicago's sparkling skyline from Lake Michigan on a sightseeing cruise. Savor a mouthwatering meal while listening to music played by a live DJ. Sip on unlimited coffee and tea while gazing out at sights like Navy Pier, Grant Park, and Willis Tower. Board the boat at Navy Pier and enjoy a personal greeting. Smile for the ship's photographer to capture the memory, then embark on an elegant dining cruise along the Chicago shoreline. After being seated at your private table, tuck into your gourmet meal. Enjoy a creative meal prepared fresh by the onboard chef. Following your meal, dance to live music or relax on any of the 3 decks as you watch the skyscrapers of Chicago's distinctive skyline glide by.  Sample Brunch Menu:Early Riser:Breakfast Pastries Scrambled EggsBreakfast Meats Breakfast Potatoes French Toast Late Risers:Kale Quinoa SaladGreen Goddess Pasta SaladCaesar Salad Oven Roasted WhitefishKid's Station Hand Carved Strip Loin Hand Carved Oven-Roasted Turkey Dessert: Cakes, Brownies, Seasons Fruit Sample Lunch and Dinner Menu: Starters (choice of one): Caesar Salad Lobster Bisque (dinner only) Jumbo Shrimp Cocktail (dinner only, available for additional price) Seafood Tower (dinner only, available for additional price) 2.5oz 1/2 Lobster Tail (dinner only, available for additional price) Main course (choice of one):Jumbo Forest Mushroom Ravioli Oven-Baked Atlantic Salmon Filet Oven Roasted Frenched Chicken Breast with Rosemary and Thyme Braised Beef Short Rib Pan-Seared Fresh Pacific Cod (dinner only) 8 oz USDA Choice Filet Mignon (dinner only, available for additional price) 18 oz USDA Prime Striploin (dinner only, available for additional price) Two 5 oz Broiled Maine Lobster Tails (dinner only, available for additional price) Dessert (choice of one): Eli's New York Style Cheesecake Duo of Sorbet Freshly Cut Fruit and Fresh Strawberries Triple Chocolate Mud Pie (dinner only) Odyssey Signature Warm Butter Cake (dinner only) French Macarons (dinner only, available for additional price) Champagne Chocolate Truffles (dinner only, available for additional price) Menu items are subject to change.

Chicago: Museum of Ice Cream Entry Ticket

5. Chicago: Museum of Ice Cream Entry Ticket

The world-famous ice cream attraction is now open in Chicago. Step into an ice cream wonderland that is bound to ignite your senses through a theatrical experience with unlimited ice cream treats as you journey through 14 installations. Ride on the pink Sprink-L line, put your golf skills to the test on the Putt-Putt course, or take a dip in a pool filled with millions of sprinkles. Come with an empty stomach and get ready to make unforgettable memories. When you finish your experience, be sure to explore the museum's whimsical shop. The Museum of Ice Cream is not a traditional museum — every installation is interactive. This means touching isn't only allowed, it's encouraged.

Chicago: Architecture Center Cruise on Chicago's First Lady

6. Chicago: Architecture Center Cruise on Chicago's First Lady

Hop onboard the only cruise narrated by Chicago Architecture Center certified volunteer docents who will share their wealth of knowledge about Chicago’s “canyon of architecture” – the Chicago River. Cruise down all 3 branches of the Chicago River, with unobstructed, open-air, 360-degree views of the city’s wide variety of architectural styles, including Art Deco, neoclassicism, mid-century modernism, and postmodernism. Discover how design shaped history and influenced life. Enjoy guaranteed seating on the open-air upper decks and purchase items at the full-service cocktail and snack bars in climate-controlled interior salons. Listen as docents share stories of over 50 buildings and 13 bascule bridges along the river, and some of the iconic figures responsible for them. If you're a non-English speaker, get access to a pre-recorded tour narration on your smartphone. Simply scan a QR code, download a mobile app, and connect it to the onboard Wi-Fi network. Narration is automatically triggered based on the location of the vessel on the tour route, so sit back and relax. You can also use your cruise ticket for discounted admission to the Chicago Architecture Center, which is just steps away from where the cruise departs. Pay just $5 compared to the normal $14 entry fee.

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

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

Enjoy spectacular views of Chicago from an MD500 helicopter. This 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.

Chicago: Seadog Speedboat Fireworks Cruise on Lake Michigan

8. 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! Join us on Wednesday and Saturday evenings during the summer months for an unforgettable memory.

Chicago: Big Bus Panoramic Sunset Tour with Live Guide

9. Chicago: Big Bus Panoramic Sunset Tour with Live Guide

From the top deck of a double-decker bus, experience Chicago at night. Enjoy a 90-minute, panoramic tour and take in unique views of the Chicago skyline, comprised of world-famous skyscrapers and revolutionary architecture. Take a photo overlooking downtown from the Museum Campus in front of the Adler Planetarium. Be amazed by the beautiful water and light display of The Buckingham Fountain as you discover the bustling nightlife of Chicago. Marvel at the magical light show of the one-of-a-kind Art on the Mart, displayed on the facade of the Merchandise Mart. See the city reflect off The Bean (Cloud Gate) at the famous Millennium Park. Experience the city that built the skyscraper, and see architectural marvels like the John Hancock Center, the Wrigley Building, the Chicago Tribune Building, and the Willis Tower. Finish your tour at Navy Pier, with the knowledge that you can continue exploring the city with confidence. From the pioneering skyscrapers to the Great Chicago Fire, this night tour will take you on a journey you won't soon forget. Be sure to soak up the exciting atmosphere that makes the Windy City such a fascinating and dynamic place.

Chicago: Fireworks Gourmet Dinner Cruise on Lake Michigan

10. Chicago: Fireworks Gourmet Dinner Cruise on Lake Michigan

Dine aboard our unique boat, the Odyssey, which is designed to provide the ultimate viewing of Chicago's sights. Dine on a gourmet three-course meal served at your private table, then dance the night away to the live band and watch the beautiful fireworks display with the Chicago skyline as a backdrop. Experience an elegant dining cruise along the Chicago shoreline aboard the luxury cruising vessel, Odyssey. Your evening starts as you are greeted aboard by the Captain and crew and our ship's photographer will take a picture to capture your memory. After being seated at your private table, enjoy your gourmet three-course meal consisting of creative appetizers and entrees prepared fresh onboard daily by our Executive Chef. The wait staff will time your meal according to your preferences so you can savor every moment of your three-hour dinner cruise. After dinner dance to the live music or relax on one of three climate-controlled decks as you watch the lights of Chicago twinkling in the night. Don't forget to visit the Captain's bridge, which is open during most of your cruise. Sample Dinner Menu:  Tasting Trio Shrimp & Watermelon  English Cucumbers | Pickled Shallots | Extra Virgin Olive Oil Roasted Summer Vegetable Salad Yellow Corn | Zucchini | Caramelized Onions | Heirloom Tomato | Arugula | Herb Vinaigrette Whipped Goat Cheese  Candied Pecan Herb Crust | Balsamic Strawberries | Crostini Entrées Jumbo Lump Crab Cakes  Sweet Corn, Red Pepper & Thyme Succotash | Cajun Cream Sauce Oven Baked Atlantic Salmon Filet  Lemon Orzo with Red Onions & Sun-Dried Tomatoes | Citrus Dill Sauce Maple & Mustard Glazed Chicken Breast  Fingerling Potatoes & Chives | Haricot Verts | Dijon Mustard Cream Sauce Braised Beef Short Rib  Idaho Potato & Horseradish Mash | Baby Carrots | Pearl Onions | English Peas | Cabernet Sauvignon Sauce Greek Zucchini FrittersV  Lemon Orzo with Red Onions & Sun-Dried Tomatoes | Spring Onion & Cucumber Tzatziki Desserts Duo of Sorbet  Seasonal Sorbet | Fresh Fruit Granny Smith Apple Parfait  Cinnamon Spiced Apples | Almond & Oat Crumble | Candied Chili Bacon Salted Caramel Cake  Dark Chocolate Ganache | Raspberry Sauce Odyssey Signature Warm Butter Cake  Vanilla Bean Ice Cream | Blackberry Sauce Menu subject to change without notice.

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What people are saying about Chicago

Overall rating

4.5 / 5

based on 70 reviews

Very great experience.You can literally see the whole entire Chicagoland from 94 stories up and I came at night for my second time visit.Would recommended.

Our boys (ages 10 & 9) were blown away by the ice cream samples in every room you entered! It was a unique and highly enjoyable experience!

It was scary at first but I had fun the whole time I was there with my husband

Loved it!!! No crowds or long lines!! Love Chicago in the winter!!

Great view and the bar/lounge was very comfortable.