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Chicago is one of the biggest and most bustling cities in all of America. Located right on Lake Michigan you've got a beautiful waterfront located right next to the heart of Chicago's downtown core. It really can't get much better than that!
While some might say that other American cities like New York, San Francisco or Miami have more to offer, Chicago has more than a few things that it does better than every other city. Chicago is known worldwide for their unique and breathtaking architecture, Chicagoans are insanely proud of their sports teams and we all know they've got their pizza on lock!
So even though the winter months get pretty cold, there's no reason not to get out there and experience some of the great things this city has to offer. Luckily, with Groupon you'll barely have to pay anything to have a great time because you'll find amazing deals all across the city this January!
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Helicopter Tour Of Chicago
Original Price: $356
Savings: $256 (28% off)
Why You Should Go: View the windy city from a unique point of view with this amazing Groupon deal! They offer daytime tours, twilight tours and private tours pairs to view the stunning city skyline from above.
Chicago History Museum Tickets
Original Price: $32
Savings: $20 (38% off)
Why You Should Go: Get a taste of Chicago's rich and vibrant past through the winding halls of it's amazing History Museum. This groupon deal offers 38% off single tickets, groups of four tickets and groups of two tickets!
Frank Lloyd Wright Home/Studio Tour
@margeauxlamourOriginal Price: $20.39
Savings: $11 (46% off)
Why You Should Go: Frank Lloyd Wright is a famous architect who designed some of America's most infamous and beloved buildings. He lived and worked in his home in Chicago and created many buildings around the city such as the Robie House, the Unity Temple, the Rookery and more.
Chicago 360 Observation Deck Admission
Price: $20.50
Why You Should Go: The 360 Chicago experience, formerly known as the John Hancock Observatory, is one of the best ways to view the city. You'll get a unique 360 view of the cities skyline. They also have options to buy their Sun & Stars ticket for day and night views or the TILT ticket for their new 'outward tilt' experience!
Pollyana Brewing Company Tour
Original Price: $50
Savings: $25 (50% off)
Why You Should Go: Take a 1 hour long tour through one of Chicago's top brewing companies. A tour for two will get four 13 oz. pours of beer to try and two take home pints and a souvenir growler!
Architectural Boat Tour
Original Price: $86
Savings: $64 (26% off)
Why You Should Go: Chicago is famous for it's unique architecture compared to the rest of America. A boat tour on the Chicago River will allow you to hear the history and view the gorgeous creations of some of the cities most amazing downtown buildings.
Chicago Bulls Tickets
@chicagobullsPrice: $31-$87
Why You Should Go: The famous Chicago Bulls basketball team are playing a total of 5 home games this January which is the perfect time to take advantage of these groupon deals. Depending on how popular the game is the price ranges but you're guaranteed great seats!
Double Decker Bus Tour
Original Price: $39
Savings: $30.99 (21% off)
Why You Should Go: Discover the city and all it's history through a fun double decker bus tour or trolley tour. You can see the city in a different light and maybe learn a few new things along the way.
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Chicago Pizza Tour
Original Price: $50
Savings: $26.50 (47% off)
Why You Should Go: This wouldn't be a Chicago food list without the famous deep dish pizza! Tour Chicago's River North neighborhood and taste some of the best pizza the city has to offer. 3 different pizza stops are included in the tour that runs every Saturday and Sunday at 1pm.
Neighborhood Wine Walk
Original Price: $120
Savings: $68.50 (43% off)
Why You Should Go: Take a wine tour through the trendiest neighborhoods. Stop at 3-4 different places to sample various red, white and sparkling wines! You'll also get cheese and meat plates to pair with your wine tastings.
Underground Donut Tour
Price: $30
Why You Should Go: This is Chicago's first ever donut tour! It lasts 4 hours and takes you to the city's top 4 donut shops. This is perfect for all the donut lovers in the city.
Four Course Thai Dinner For Two
Price: $78.50
Why You Should Go: This amazing deal offers couples a luxurious four course meal at Herb Restaurant in the North Side. The dinner comes with a starter, a soup, an entree and a dessert that is perfect for a special night or an anniversary dinner.
World Cuisine Food Tour
Price: $69
Why You Should Go: This world fare tour takes place in Chicago's Wicker Park area and features some delicious cuisines. Go from American BBQ to Korean noodles and dumplings to Middle Eastern food and more! The tour will last 2 hours and is a great way to explore the foodie scene in Chicago.
Pajama Bar Crawl
Original Price: $24.91
Savings: $12 (52% off)
Why You Should Go: This an annual pub crawl that takes place in Chicago that's fun for literally everyone involved. Wear your pajamas and visit some of the best bars in the city. Upload pictures throughout the event and at the end a panel of judges will choose a winner!
Italian Food Tour Of Chicago
Price: $50
Why You Should Go: Try some of the city's best Italian foods on this fun tour. Walk past some of Chicago's famous landmarks and enjoy foods like deep dish pizza, arancini, gelato and more!
Bourbon Tasting Experience
Original Price: $65
Savings: $45 (31% off)
Why You Should Go: On January 18th the Irish pub Ballydoyle in Aurora is offering a Bourbon tasting event! Sample 5 different Bourbons paired with 5 small plates. The event also includes an education by the pub's whiskey ambassador.
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60-Minute European Facial
Original Price: $150
Savings: $39 (74% off)
Why You Should Go: The Skinsational Advanced Skincare spa in Roscoe Village is offering an insanely good deal on facials! Enjoy a rejuvenating facial in a relaxing environment with exceptionally clean facilities.
30-Minute Foot Reflexology Massage
Original Price: $60
Savings: $16 (73% off)
Why You Should Go: The DQ Luxury Reflexology & Relaxation Retreat in downtown Chicago is offering a crazy good deal on their reflexology massages. Reflexology says that the feet hold the key to improving function in your entire body. So, with a reflexology massage you can see the benefits each pressure point on your foot will have on different parts of your body.
6 Laser Hair Removal Treatments
Original Price: $750
Savings: $129 (83% off)
Why You Should Go: Laser hair removal is becoming increasingly popular as a hassle-free hair removal practice. The Lincoln Park Aesthetics is offering an amazing deal up to 83% off 6 laser treatments varying in price depending on whether you want a small, medium or large area of hair removed.
Spa Mani-Pedi Package
Original Price: $45
Savings: $32 (29% off)
Why You Should Go: Everyone deserves to treat themselves to a mani-pedi spa package from time to time. This is an amazing deal from Forever Beauty in Mckinley Park that gets great reviews from clients online.
Highlights, Haircut and Blowout
Original Price: $165
Savings: $79 (52% off)
Why You Should Go: Zazu Salon near the North Side of Chicago is offering an amazing deal on their special services. Get highlights or belayage, a haircut and a blowout for such a reduced price! The reviews at this salon are all amazing too so you know you're going to walk out looking like a movie star.
Swedish Or Deep Tissue Massage
Original Price: $125
Savings: $89 (29% off)
Why You Should Go: The Licoln Park Massage Spa is offering amazing discounts on their 90, 75 or 60 minutes deep tissue or Swedish massages. Feel extremely relaxed in this clean and friendly spa environment.
Teeth Whitening Session
Original Price: $200
Savings: $48 (76% off)
Why You Should Go: Smile Great located in Oak Park is offering an amazing deal on their teeth whitening services. Get a 30 or 60 minute session to remove the stains from your daily cup(s) of coffee!
60-Minute Couples Massage
Original Price: $160
Savings: $99 (38% off)
Why You Should Go: Mirror Mirror Spa Salon located in downtown Chicago is offering an amazing deal on their popular couple's massages. The massage offers a 60 minute Swedish massage session to leave you and your S/O extra relaxed!
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60 Day Membership To Daily Burn
Price: Free!
Why You Should Go: Daily Burn, an online site of workouts available for streaming, is giving out free 60-day memberships! Get fit, fast with these amazing workout videos available for use right in your own home.
Four Indoor Cycling Sessions
Original Price: $85
Savings: $39 (54% off)
Why You Should Go: This amazing deal of 4 indoor cycling classes is available at CycleBar in Fulton Market. Reviews say the classes are always an amazing workout and super fun at the same time.
Barre Classes
Original Price: $120
Savings: $39 (68% off)
Why You Should Go: The Pure Barre Lincoln Square is offering 5, 10 or 20 packs of barre classes for such a great deal! Barre classes give you an amazing workout that combines ballet, yoga and pilates moves that will kick your butt, literally!
Unlimited Boot Camp Classes
Original Price: $100
Savings: $25 (75% off)
Why You Should Go: These intense boot camp classes are given by Hustle Fitness in North Side, Chicago. You can either choose the 14 day unlimited boot camp classes or the 21 day rapid fat loss program to get into shape fast!
Gym Membership With Personal Training
Original Price: $75
Savings: $39 (48% off)
Why You Should Go: Get a one month gym membership to Southport Fitness at a super reduced price. The membership also comes with personal training sessions to get you set up with a workout plan suited to you.
UltiFit Obstacle Course Fitness Gym
Original Price: $75
Savings: $29 (61% off)
Why You Should Go: Get fit with this intense but fun way of working out. UltiFit combines obstacle course training with functional fitness moves for a unique class! You can get 5, 10 or 20 passes for 61% or more.
Rock Climbing Passes
Original Price: $72
Savings: $45 (38% off)
Why You Should Go: Get a day pass for two, an intro to climbing class or a two hour learn the ropes and day pass from Brooklyn Boulders. Get a workout while having fun at this cool rock climbing spot in the city.
Unlimited Boot Camp Classes
Original Price: $297
Savings: $49 (84% off)
Why You Should Go: With On The Go Bootcamp in River West, Chicago you can get 21 days of unlimited classes to their rapid fat loss boot camp sessions. Get a really good workout in a fun and intense atmosphere.
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Japan And China Tour
Price: $1,799
Why You Should Go: This once in a lifetime trip will take you to Japan and China including hotels, air fare and daily breakfasts! Visit big cities like Tokyo, Beijing, Kyoto and more on this super deal of a trip.
Omni Fort Worth Hotel Texas
Original Price: $188/night
Savings: 119/night
Why You Should Go: Take a vacation in the heart of downtown Fort Worth, Texas. Stay in a luxury room, eat at their numerous dining options, swim in their heated outdoor pool, relax at their luxurious spa, and explore the downtown area!
Italy Vacation
Original Price: $1,267
Savings: $899 (30% off)
Why You Should Go: This 8-10 day vacation to the gorgeous country of Italy includes air fare and hotels! Visit places like the Amalfi Coast, the historic city of Rome and the rolling hills of Sorrento.
7 Day Iceland Vacation
Price: $899
Why You Should Go: Visit the capital city of Reykjavik, Iceland and see some of the world's most beautiful landscapes. Soak in the famous Blue Lagoon, take a trip to see the famous waterfall Gullfoss and so much more!
England And Ireland Vacation
Original Price: $1,399
Savings: $999 (29% off)
Why You Should Go: Take a 6-8 night trip to England and Ireland to see some beautiful and historic attractions. This is includes round trip air fare, hotels and breakfast while you're there.
All-Inclusive Dominican Republic Vacation
Price: $599
Why You Should Go: Take a 4-7 beach vacation to the beautiful Dominican Republic! This all-inclusive trip includes air fare, hotel stay, all meals and beverages and daily and nightly entertainment. Lounge your days away on the white sandy beaches and experience the natural water life around you.
Premium Dubai Vacation
Price: $899
Why You Should Go: Experience the bustling and lively city of Dubai on this premium vacation. Your flight and luxury accommodations are included in your trip and you can visit the exciting markets, belly dancing performances, and more!
All-Inclusive Cancun Resort
Price: $429
Why You Should Go: Take a trip to the beautiful and relaxing Cancun, Mexico on an all-inclusive trip! Your flights, meals and accommodations are all included in the trip plus the resort has it's own waterpark.
Luciano Frattolin is taken away in custody from the Essex County Court in Elizabethtown, New York on Friday, July 24, 2026. Luciano Frattolin charged with 2nd-degree murder and concealment of a human corpse.
THE CANADIAN PRESS/Christopher Katsarov
Police officers open the back of a recovered truck during a press conference regarding Project 24K, a joint investigation into the theft of gold from Pearson International Airport, in Brampton, Ont., on Wednesday, April 17, 2024.
THE CANADIAN PRESS/Arlyn McAdorey
The Rockyview General Hospital is pictured in Calgary, Thursday, March 20, 2025.
THE CANADIAN PRESS/Jeff McIntosh
This composite image shows, left to right, B.C. NDP Leader David Eby in Vancouver, on April 13, 2026; B.C. Conservative interim Leader Lorne Doerkson, in Vancouver, on Sept. 22, 2026; B.C. Green Party Leader Emily Lowan in Victoria, on Sept. 23, 2026.
THE CANADIAN PRESS/Darryl Dyck, Rich Lam, Kevin Light