8 Things To Do in Chicagoland This Winter

This list of things to do in Chicago, IL will keep you and the kids busy and cabin-fever free this Winter!

Winter is tough with kids. I’m sure some of you die hards will disagree, but for me it takes so much more effort to get out of the house: coats, gloves, hats, taking off coats for carseats, defrosting the car. And the list goes on. But I’ve put together a list of kid-friendly things to do around Chicagoland area that will make all the effort worth it! Good luck!

8 Things to do with Kids in Chicago, IL this Winter:

1. Visit an outdoor ice rink!

• • • Rosemont Skating In The Park
      • Now through February 28th
      • “Admission to the Chicago Wolves Ice Rink is FREE, however a credit card is required to hold reservations. Bring your own skates or rent skates online for $8. Guests with reservations who fail to appear for their skating time will incur a $8 per person fee. Refunds will be given to guests with reservations that are cancelled due to rink closure caused by inclement weather or COVID-19 mandates. In order to ensure social distancing this year, the outdoor ice rink will limit capacities and advance ice skating reservations are required. 45-minute skating time slots can be reserved and ice skate rentals can be made using the link below.”
      • Face masks encouraged, required for staff.
    • Maggie Daley Park Ice Skating Ribbon
      • Skate rental – $16; Skate with your own skates – $5
      • Reservations required to skate
    • McKinley Ice Rink
      • 2210 W. Pershing Rd, Chicago
      • Admission is free, skate rental is $7
      • “There will be a 50-person occupancy limit at the rink. Admittance will be first come, first served. Warming buildings will be accessible to the public for skate rental only. Expect additional wait times for entry, skate rental, and cleaning. As with all other park spaces, masks are mandatory while skating, and social distancing must be observed at all times. No more than two (2) people may skate together.”
    • Wentworth Ice Rink
      • 5625 S. Mobile Ave
      • Admission is free, skate rental is $7
      • “There will be a 25-person occupancy limit at the rink. Admittance will be first come, first served. Warming buildings will be accessible to the public for skate rental only. Expect additional wait times for entry, skate rental, and cleaning. As with all other park spaces, masks are mandatory while skating, and social distancing must be observed at all times. No more than two (2) people may skate together.”
    • The Winter Wonderland Ice Rink in Orland Park
      • 15600 West Avenue & Fun Dr.
      • Admission is $3
      • Reservations to skate can be made up to 5 days in advance online
    • Warren Park Blackhawks Ice Rink
      • 6601 N. Western Ave
      • “This winter, the ice rink will operate (weather permitting) from Thanksgiving weekend (Friday) until February. Call (773) 761-8663 for skate fees, times, and rental information. If it gets a little chilly…no worries we have a toasty warming house. Restrooms are also available at the rink.”

*Many local parks and towns will have natural rinks where you bring your own skates and there is no one monitoring or maintaining the rink. Just watch the weather to determine when the ice will be frozen!

2.  Keep the holiday spirit going by making a reservation at a holiday, pop – up, restaurant experience

• • Snag reservation at Santa Baby
    • A multi-room, multi-level, christmas experience open through January!
    • It’s not just for adults! Kids and parents alike will enjoy this Christmas experience in Wrigleyville
    • All seating is considered outdoor seating – regulations allow us to offer a tented patio (with heaters!) and indoor dining tables next to open air windows. Dress for the weather and the season!
  • JoJo’s Shake Bar Winter Wonderland
    • “Tis’ The Season with JoJo’s Winter Wonderland. Launching November 16th, JoJo’s is bringing a 5,000 sq ft outdoor Winter Wonderland to Downtown Chicago. This incredible food and beverage experience will feature JoJo’s over the top holiday treats including Baked Hot Chocolate, Santa’s Milk & Cookie Flights, Spiked Ciders, Biggie Hot Chocolates and The Winter Wonderland Shake, a Peppermint Shake topped with a Christmas Tree Cookie, Snowman DoDo & Marshmallow Presents. The Winter Wonderland experience takes place in our heated outdoor dining pavilion.”
    • Open daily 11 AM – 10 PM through February 1st

 3. Head to the drive in!

• • Chitown Movies
    • We had a blast at this drive in movie theatre in Pilsen this summer. Turn the heat on and the headlights off for a fun movie experience this winter!
    • Food delivery ordered from your phone & delivered straight to your car!
  • Obscurity Brewing Drive-In
    • 113 W. North St, Elburn
    • Full car hop service with food and drink right to your car!
    • Movie list scheduled through mid February!
  • Rock Island Public House Drive In
    • The movie selections are not necessarily younger children friendly, however, parents need a date night even in a pandemic!
    • Enjoy free screenings every Fri – Sun on a first come, first serve basis.
    • Food and drinks available for purchase!
    • You’ll love the unique movie selections!

4. Go sledding!

• • Dan Ryan Woods (Chicago)
    • S Western Ave & W 87th St
    • Call 773-233-3766 for sledding hill status.
    • This sledding hill has lighting and staff when open Sunday – Thursday: 10am – 7:30pm; Friday-Saturday: 10am – 8:30pm daily when conditions allow
    • There is a separate area just for snowboarders!
  • Caldwell Woods (Chicago)
    • W Devon Ave & N Nagle Ave (hill is on the Devon side)
    • Call 847-647-2240 for sledding hill status.
    • This hill has lighting and indoor bathrooms
  • Soldier Field (Chicago)
    • Don’t count on this 35 ft. sledding hill always being open but when Chicago gets 4-5 inches of snow and the forecast calls for multiple days of freezing temps, the kids will get a kick out of sledding next to the famous football field!
    • Call (312) 235-7000 for sledding hill status.
  • Horner Park (Chicago)
    • 2741 W. Montrose
    • You’ll find a great slope on the corner of Montrose & California
  • Humboldt Park (Chicago)
    • You will find the sledding hills west of the fieldhouse near the lagoon
  • Warren Park (Chicago)
    • 6601N. Western Ave
    • Great sledding hill for younger children since there are stairs on either side of the hill and a nearby warming house. Also plenty of parking!
  • Blackwell Forest Preserve (Warrenville)
    • “On weekends and school holidays December – February when there’s plenty of snow on Mount Hoy at Blackwell Forest Preserve (usually more than 3 inches) you can take a fun 800-foot ride down the hill. Inner tube rentals are at the base of the hill and are $10 per tube per day. Only District tubes are allowed.”
    • The tubing hill is open 10AM – 4 PM with rentals ending at 3:30 PM
  • Riverwalk Sled Hill at Rotary Hill (Naperville)
    • “There is great sledding right on the Naperville Riverwalk. The hill provides fun for the entire family. Sledders should bring their own inner tubes or plastic sleds. Wooden sleds and metal-runner sleds are not permitted. The hill closes at 9:00 p.m. except on Fridays and Saturdays, when it remains open until 10:00 p.m.”
  • Weigand Riverfront Park (Naperville)
    • “The hill at Weigand Riverfront Park may be used only as a snowboarding hill. Snowboards are restricted on all other Park District hills. Sledding is not allowed at Weigand Riverfront Park. Please note that snowboarders assume full risk and responsibility for determining that all conditions are safe for snowboarding. The snowboarding hill at Weigand Riverfront Park closes at dusk.”
  • Techny Prairie Park and Field (Northbrook)
    • “The popular sled hill remains from the former Meadowhill Park South, along with a warming house, stairs and lights for evening use. The hill measures 28 feet in height.”
  • Century Park (Vernon Hills)
    • Ice Rinks and Sled Hill
      Monday – Sunday: 7:30 am – 9:00 pm.
      *Lights around the rink and hill automatically turn off at 9:00 pm
    • Warming Shelters
      Saturday and Sunday: 1:00 pm – 9:00 pm
      *Only available if either the ice rink and/or sled hill are open
    • A limited supply of loaner ice skates are available on weekends from 1:00 pm – 9:00 pm when the ice rink is open. They will be given out on a first-come, first-served basis. Hot drinks and candy are also available for purchase.
  • Caboose Park (Lake Villa)
    • 27908 Fairfield Rd
    • “For your recreational pleasure the toboggan and sled hill at “Caboose Park” will be lit for evening use between the hours of 5:30 and 10:00 p.m., weather and conditions permitting. Easy access can be gained from the Grand Avenue parking lot.”
  • St. James Park / Mt. Trashmore (Evanston)
    • This former landfill holds a massive hill (where sledding is actually off limits) however the surrounding smaller hills are open for sledding!
    • Dodge Ave. & Mulford St.

5. Enjoy a winter themed dessert!

• Bang Bang Pie & Biscuits
  • Both locations are closed due to the pandemic except for preorder through their online pantry for contactless pickup in Logan Square
  • (Reopening Jan 15th)
• Firecakes Donuts
  • Seasonal donuts include: Malted Milkball and Valrhona Chocolate
  • No one will judge you if you make it a Donut Ice Cream Sandwich either. Consider it a prescription for 2020/21
• First Slice Pie Cafe
  • Did you know that Food & Wine voted First Slice as one of America’s BEST apple pies?!
  • In addition, First Slice served more than 37,000 meals in 2007, and currently serves close to 4,000 meals each month to Chicago’s hungry, every month.
• Floriole
  • Open Wed – Sun
  • Dying to try the Galette des Rois and Gingersnap Lime Pie
• Beatrix 
  • The Oh My! Caramel Pie will have your mouth watering and you ordering seconds.
• Blue Sky Bakery & Cafe
  • “Blue Sky does more than create sweet and savory pastries made with the freshest, highest quality ingredients. As a nonprofit organization, we also raise the edible consciousness of our community by providing transitional employment to homeless and at-risk youth.”
  • Pumpkin pecan scone with a side of social justice please!
• BomboBar
  • You are just going to drool over BomboBar’s fall menu! If the salted caramel hot chocolate and caramel apple cider wasn’t enough already, there’s the pumpkin pie marshmallow and apple caramel gelato to sweep you off your feet.
• Brown Sugar Bakery
  • The most famous and tastiest caramel cake in Chicago! Don’t sleep on this amazing bakery.
• Do-Rite Donuts
  • I’ll take my pumpkin spice in donut form thank you very much. With a Michigan apple fritter on the side. :p
• DMK Burger Bar
  • Skip the campfire and head straight to DMK for a toasted marshmallow shake. Hard day monitoring the e-learning? Make it a boozy shake! 😉
• Glazed And Confused
  • Try a donini! Pressed like a panini, served on a classic cake donut!
• Goddess And The Baker
  • Treat yourself to a Pumpkin Apple Butter Latte before exploring the rest of their delicious menu!
• Hoosier Mama Pie Company
  • (Reopening January 15th)
  • Make sure to order a pear apple cranberry pie, you won’t regret it!
• Jeni’s Splendid Ice Creams
  • Known for the unique ice cream flavors you can be guaranteed for some wintry picks here!
  • Brandied banana brûlée anyone?
• Jo-Jo’s Shake Bar
  • Until February 1st, JoJo’s outdoor patio is converted into an adorable winter wonderland! Enjoy winter themed shakes and biggie hot chocolates, as well as their normal menu!
  • The igloos  are are available on a first come, first serve basis!
• Katherine Anne Confections
  • Upgrade from your regular old chocolate with a creamy cup of Katherine Anne’s drinking chocolate!
  • The salted caramel will definitely be the right flavor for the season
• Kilwins
  • There are multiple locations around Chicagoland but the Hyde Park location is African American owned and operated, so we like to support them whenever we can!
  • You will find yourself drooling over the caramel apples and chocolate confections but my absolute favorite flavor of ice cream from Kilwins is their Perfect Apple Pie flavor. I look forward to this returning to their menu every year!
• Mindy’s Bakery
  • The famous Mindy Segal will be selling to go hot chocolate on the weekends!
  • Forget winter, I would drink this delectable cocoa in the heat of the summer if I could!
• Molly’s Cupcakes
  • The winter cupcake flavors are back in season and I am here for it!
  • Don’t miss out on the German chocolate cake & Tiramisu for January!
• Pie, Pie My Darling
  • 100% Vegan sweets baked from scratch!
  • You can find their cakes by the slice (while supplies last) for delivery and pickup at Uptons Breakroom in West Town & The Handlebar in Wicker Park. The flavor changes every other week, so check their menus/ instagram for this week’s flavor.
  • E-mail to inquire about ordering a whole cake!
• Pretty Cool Ice Cream
  • Special pops, pints, and more made in festive flavors for the winter holiday season
  • (The key lime pie flavor is my favorite no matter what the season!)
• Sweet Mandy B’s
  • The snickerdoodle cupcake is a personal favorite of mine!
• XO Marshmallow
  • The World’s FIRST Marshmallow Café is right here in Chicago!
  • Their s’mores menu is fantastic! Plus, hot chocolate, marshmallow latte, pumpkin spice marshmallows, and more!
• Xurro
  • The yummiest Churros with a creative spin!
  •  The Peppermint Christmas milkshake is the reason for the season.

6. Book a Chicago staycation and reserve a pool time slot!

*Make sure to call ahead to determine the rules surrounding the pool and verify it’s availability

• • Hyatt Centric
    • After booking with the central reservation line, contact the front desk to book your pool reservation.
    • The reservations are for 45 min time slots
  • The Hilton at McCormick Place
    • Private only pool times available on weekends only
  • The Peninsula
    • The pool can be booked for one hour, once a day
  • The Waldorf Astoria
    • Pool reservations for 90 min, no more than 2 families
  • Aloft in Rosemont
    • Pool time slots available in 60 min increments
  • AC Hotel by Mariott
  • Westin Rosemont
  • The Ridge at Lake Geneva
    • Hop over the border and enjoy the beautiful hotel, grounds, and pool.
    • While you are there make sure to book an igloo for dining, and visit the Ice Castles when they open mid January!
  • The Intercontinental
  • The Langham Chicago
    • “Lounge furniture has been re-arranged according to local social distancing recommendations and are sanitized after each use. High-touch areas will be sanitized hourly.”
  • Great Wolf Lodge Gurnee
    • Save up to 40% with code GETAWAY if you book before Jan 17th and stay before March 11th
    • Every nights stay contains two days of play.
    • All queues will be 6-feet and managed by staff, especially in waterpark​
    • All seating will be 6 feet apart across waterpark, F&B, ​public areas
  • Holiday Inn Express (Hoffman Estates)
    • When checking in, you can reserve individual time slots for your family at 40 min a time.
  • Marriott Suites (Downers Grove)
    • 2 hr private pool reservations that you can reserve as soon as you book.
  • Hyatt Lodge Oakbrook
    • Pool available with limited occupancy
  • Renaissance Hotel – Schaumburg
    • “Indoor Pool & Outdoor Pool Patio is key access only to limit interactions of guests in this space. Guests interested in swimming can sign up for a 1.5-hour swim segment. Each swim segment will be followed by a .5 hour cleaning. This will include water filtration, towel replenishment, cleaning and sanitizing.”
  • Timber Ridge Lodge & Waterpark at Grand Geneva
    • “When you stay at Timber Ridge Lodge, you receive four free waterpark passes with a one-bedroom suite, and six passes with a two-bedroom suite.”
    • Throughout the waterpark you will notice social distancing signage and floor markers placed throughout the waterpark.
    • Clear protective screens have been placed where regular interaction with resort associates occurs such as the bag check and towel desk.
    • Guests enjoying mini-golf will find staggered tee times to allow for social distancing.
  • Comfort Inn & Suites Galena
    • Big water slide and area for smaller kids.
    • Close to skiing and fun outdoor adventures!

7. Eat in an igloo or cute dining hut!

• • Giannis Cafe
    • Locations in Kildeer & Palatine
    • Call to make a reservation in their igloo village
    • “We are a family owned and operated, Full service Italian Restaurant. For over 17 years we have been serving some of the freshest seafood, pasta and other Italian entrees in the Chicagoland area.”
  • Kuma’s Corner
    • Heated outdoor dining at all of their Chicagoland locations!
  • Formentos
    • Make a reservation for their heated patios / snow globes!
  • Beatrix
    • Igloo and greenhouse dining options!
  • Tanoshi Sushi
    • “We have individual greenhouses available for our outdoor dining. COVID-19 has put a big strain on small restaurants, but we want to continue serving customers with minimal risk. Each individual greenhouse is heated and ventilated, and sanitized/aired out between customers. Make a reservation by calling, or through OpenTable.”
  • Tavern on Rush
    • Call 312-664-9600 to reserve an igloo!
  • Somerset by Viceroy Hotel Chicago
    • “For the ultimate winter dining experience, book a reservation in our heated outdoor Greenhouses.”
  • Granite City Food & Brewery
    • Schaumburg location has heated tents
  • The Melting Pot
    • The outdoor huts at the Schaumburg location are semi-private
  • Fiamme
    • Naperville
    • All reservations guarantee a winter villa or greenhouse
  • Solemn Oath Brewery
    • “Our brewery features a 4200+ SF outdoor beer garden with tables 8-12 feet apart featuring our freshest beers and seltzers. Dome deposits will be applied to the bill during your visit.”
    • 90 min reservation for up to, but no more, than 6 guests.
  • The Assembly American Bar & Cafe
    • Hoffman Estates
    • Call 847-843-3993 and reserve a dining hut for an adorable and safe dining experience!
    • The dining huts hold 4-6 people max and can only be reserved for 90 min.
  • The Drake Hotel 
    • Oakbrook
    • “Select from four private and fully enclosed igloos, all with a unique theme. Each igloo has a small heater for your comfort, but we suggest bundling up if it’s cold. Igloos seat up to 8 guests, but during the current government mitigations, igloo seating will be capped at 6 guests.”
    • There is a $200 minimum after 5 PM Sun – Wed and it goes up to $300 Thurs – Sat. But all us moms know it’s better to take the kids to dinner early when eating out!
  • Aurelio’s of Geneva
    • Geneva
    • Reservations required at dinner time
    • Closed on Mondays
  • Bien Trucha
    • Geneva
    • “Is there anything more fun than enjoying our tacos and drinks in your own outdoor pod under the sun, stars, or falling snow?!!
    • “Pods will be available for 1.5 hr. increments and will have no minimum at lunch and a minimum of $50 Sun-Thu and $125 Sat & Sun for dinner.”
    • Ask about kid menu options in person
  • Livia Italian Eatery
    • Geneva
    • To reserve the igloo tents at the Geneva location, you must call 630-402-6444
  • Ivy
    • Wheaton
    • “Whether you are interested in having a full dining experience, or an opportunity to enjoy wine, cocktails, and conversation with 4-8 of your closest friends or family members, the Ivy Igloo is the perfect winter setting.”
    • With a maximum capacity of 8 people, the rental fee is $100 and the minimum is only  $400 for dinner, $300 for lunch.
  • The Hen House of Wheaton
    • Wheaton
    • “We have heated Igloos and a heated tent, Igloos are by reservation only, call (630)480-0611.”
    • Hours: 7 AM – 2:30 PM
  • Wine Thief
    • Frankfort
    • Bring the family for a snow globe visit! Hot cocoa bombs, kid food, and games!
    • No food and beverage minimum on bookings between 11 AM – 2:30 PM
  • The Lucky Monk
    • S.Barrington
    • “We look forward to hosting you like we have never hosted you before. Book your Sanctuary Experience in one of our 4 private Igloos for up to 6 guests. Each Igloo is set with seating for 6, personal bluetooth speaker, a heater and will be served by our experienced TLM Ambassadors. Order from our regular menu or choose from our Exclusive Sanctuary Add Ons. All reservations are limited to 2 hours and no outside food or beverages will be permitted. Please come prepared for the elements.”
    • $200 Food and Beverage Minimum Fridays & Saturdays
      $150 Food and Beverage Minimum for all other reservations
  • Digs on Canal
    • Lemont
    • “Each igloo has a heater and is ventilated. Time slots are set at 90 minutes, allowing our staff to clean and sanitize the igloos prior to the next reservation.
    • We do require a deposit when you make your reservation. The deposit will be used for your food and beverage choices while you are dining in the igloo (90 minute maximum, +taxes and fees).”
  • Hacienda Real
    • Yorkville
    • Please inquire about reservations for the heated, outdoor, igloos by calling the restaurant directly at (630) 882 9541
  • Hometown Coffee & Juice
    • Glencoe
    • Hometown Houses are available to privately rent for a fee with advance reservations. Unrented Houses are available on a walk-in basis at no charge.
    • Houses are heated and can accommodate up to 6 guests at a time. Each house is cleaned, disinfected and sanitized between reservations and well ventilated.

8. Enjoy an outdoor adventure!

• • The Ice Castles
    • Lake Geneva, WI
    • “Ice Castles is an award-winning frozen attraction located in four cities across North America. The experience is built using hundreds of thousands of icicles hand-placed by professional ice artists. The castles include breathtaking LED-lit sculptures, frozen thrones, ice-carved tunnels, slides, fountains and much more.”
  • The Forge
    • Lemont
    • “Don’t stay cooped up indoors this winter. Come out and play!  With Forgefire Globe Dining, ice skating, laser tag, winter lights, and climbing towers to explore, the possibilities for outdoor fun are endless.”
  • Troll Hunt at The Morton Arboretum
    • Timed-entry tickets are required for all members and guests and will help ensure paced arrivals and moderated attendance numbers.
    • “Journey through our far-reaching forest to hunt for six colossal trolls crafted from reclaimed wood by Danish artist Thomas Dambo. Marvel at these 15- to 30-foot-tall (and one 60-foot long) sculptures that have been created to serve as protectors of our environment.”
  • Chicago Mural Hop
    • Chicago Mural Hunt
  • Suburban Mural Hunt in the West and Far West Suburbs
    • This awesome round up is courtesy of my friend Families On The Fox!