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Getaways from Chicago · Winter 2026–27

Winter getaways from Chicago

Sixteen ways out of Chicago between December and March, from a 71-minute South Shore Line ride to the Indiana Dunes to a flight of just over two hours to Mardi Gras. Each is sorted by how you get there, with the event worth timing it for, where to stay and one thing to know before you go.

  • 16trips
  • 7by car
  • 5by train
  • 4by air
  • Facts checked 21 October 2026

16 winter trips from Chicago, sorted by how you get there: 7 by car, 5 by train and 4 by air. The quickest to reach is Lake Geneva, 1 hr away; the longest trip is Detroit, 5 hr 45 min. Each one lists the travel time, the dates worth timing it for and where to stay.

At a glance

GetawayFrom ChicagoBest forTime it for
Lake Geneva 1 hr Festival, Ski, Spa Lake Geneva Winterfest, 3–7 Feb 2027
Harbor Country 1 hr 30 min Romantic, Food & wine, Outdoors January and February for sledding on the dunes and quiet tasting rooms
Kohler 2 hr Spa, Romantic, Family Frozen Fairways, 3 Dec 2026 – 28 Feb 2027
Starved Rock 2 hr Outdoors, Family, Romantic January and February, after a cold snap, when canyon waterfalls can freeze
Saugatuck & Douglas 2 hr 30 min Romantic, Culture, Festival A Christmas Carol, 11–20 Dec 2026
Galena 3 hr Festival, Romantic, Ski Night of the Luminaria & Living Windows, 12 Dec 2026
Door County 4 hr 15 min Outdoors, Festival, Romantic WinterFest, Fish Creek, 6–7 Feb 2027
Indiana Dunes 1 hr 11 min Outdoors, Family January and February, after the 3- to 4-inch snow base the park recommends for skiing
Milwaukee 1 hr 39 min City break, Culture, Festival Milwaukee Holiday Lights Festival, 19 Nov 2026 – 1 Jan 2027
Wisconsin Dells 3 hr 33 min Family, Ski, Outdoors Any winter weekend
St. Louis 4 hr 46 min City break, Festival, Culture Garden Glow, 14 Nov 2026 – 2 Jan 2027
Detroit 5 hr 45 min Culture, City break, Food & wine Detroit Auto Show (2027 dates TBA)
Nashville 1 hr 25 min Festival, City break, Family A Country Christmas at Gaylord Opryland, 6 Nov 2026 – 2 Jan 2027
Minneapolis & Saint Paul 1 hr 28 min Festival, City break, Food & wine Saint Paul Winter Carnival, 28 Jan – 7 Feb 2027
Toronto Passport 1 hr 41 min City break, Food & wine, Culture Winterlicious (2027 dates TBA)
New Orleans 2 hr 14 min Festival, Food & wine, City break Carnival season and Mardi Gras, 6 Jan – 9 Feb 2027

By car 7 trips

1 hr
Photograph · Grand Geneva Resort & Spa / Visit Lake Geneva
Walworth County, Wisconsin, USA

Lake Geneva

About an hour by car, per Travel Wisconsin; Visit Lake Geneva puts Chicago 83 miles away

Lake Geneva Winterfest puts 15 snow sculptors on the lakefront at Riviera Plaza and Flat Iron Park for five days in February, free to watch, with bonfires on the beach and an ice sculpture walk downtown. Grand Geneva has its own ski hill, so the same weekend works for a family or a couple.

Time it for Lake Geneva Winterfest 3–7 Feb 2027

The 32nd Winterfest and America's Snow Sculpting Invitational, with 15 artists from the U.S. and abroad working on the shore of Geneva Lake; free to attend.

Do
  • The Mountain Top at Grand Geneva 20 downhill runs, a six-acre terrain park and night skiing at the resort's own hill.
  • Wilmot Mountain 25 named runs, 11 lifts, terrain parks and a tubing hill, per Visit Lake Geneva.
  • Lakeside igloo dining Heated igloos at Grand Geneva ($75 weekdays, $100 weekends and holidays, 90-minute slots), Pier 290, Maxwell Mansion and others; opening dates vary by property and depend on the weather.
Stay
  • Grand Geneva Resort & Spa 358 rooms on 1,300 acres, listed by Visit Lake Geneva as AAA Four-Diamond, with the WELL Spa + Salon, its own ski hill and restaurants including Geneva ChopHouse and Ristorante Brissago.
  • The Abbey Resort & Avani Spa 334 rooms plus two-bedroom villas in Fontana-on-Geneva Lake, billed as the only full-service resort on the shores of the lake, with the Avani Spa and seasonal skate rentals.
  • The Geneva Inn 37 rooms, including whirlpool suites, set directly on the shore of Geneva Lake, with the Oak & Oar restaurant and bar.

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Winter tip Winterfest sculptors work from Wednesday to Saturday, so arrive on Saturday 6 February 2027 to see finished pieces; igloos book in 90-minute slots, so reserve one with the room.

1 hr 30 min
Photograph · TCP04 / Wikimedia Commons (CC BY 4.0)
Southwest Michigan, USA

Harbor Country

About 90 minutes by car from downtown Chicago, per the Harbor Country Chamber of CommerceAmtrak's Wolverine stops at New Buffalo: the 6:45 a.m. from Chicago arrives at 9:04 a.m. local time (Michigan is an hour ahead), per the Amtrak timetable. The South Shore Line runs to Michigan City, about 10 minutes south of New Buffalo.

Harbor Country's nine lakeshore towns, from New Buffalo to Three Oaks, sit about 90 minutes from downtown Chicago, and in winter the draw is open tasting rooms, sledding on the Warren Dunes and small inns with fireplaces. Amtrak stops in New Buffalo, so a car is optional.

Do
  • Warren Dunes State Park Sledding on the Mega Snow Hill and the Tower Hill dune.
  • Winter wine tasting Tasting rooms on the Lake Michigan Shore Wine Trail stay open through winter, including Round Barn and St. Julian in Union Pier.
  • Harbert Park skating Outdoor skating; rentals must be reserved through Chikaming Township.
Stay
  • Goldberry Woods Eight inn suites, three cottages and two vintage Avion campers on 30 acres along the Galien River in Union Pier, with gas fireplaces in the suites and a heated pool and hot tub open year-round.
  • The Inn at Union Pier 16 adults-only rooms, 12 of them heated by antique Swedish kakelugn tile stoves, an outdoor hot tub and the beach about three minutes away.

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Winter tip Michigan runs an hour ahead of Chicago, so the Wolverine's 9:04 a.m. arrival in New Buffalo is 8:04 a.m. Chicago time, an hour and 19 minutes after leaving Union Station.

2 hr
Photograph · Asher Heimermann / Wikimedia Commons (CC BY-SA 4.0)
Sheboygan County, Wisconsin, USA

Kohler

About 2 hours (150 miles) north by car, per Destination KohlerDestination Kohler puts the village an hour (55 miles) north of Milwaukee, which Amtrak's Hiawatha reaches from Chicago in about 1 hr 30 min to 1 hr 40 min.

The American Club, opened in 1918 to house Kohler's newly arrived immigrant workers, anchors a spa weekend around the Kohler Waters Spa, which the resort calls its five-star flagship. This winter the Blackwolf Run golf course turns into Frozen Fairways, with skating, sledding and snowshoeing free for overnight guests.

Time it for Frozen Fairways 3 Dec 2026 – 28 Feb 2027

Blackwolf Run's winter village of ice skating, sledding, snowshoeing and holiday lights; free for overnight guests.

Do
  • Frozen Fairways at Blackwolf Run Ice skating, sledding, snowshoeing and holiday displays, Thursday to Sunday; free for overnight guests.
  • Kohler Waters Spa The resort's spa; The American Club's adults-only Carriage House has direct spa access.
  • Afternoon tea at The Wisconsin Room Festive tea service until 2 January 2027, then afternoon tea Thursday to Saturday, 12:30 to 2:30 p.m., to 9 May.
Stay
  • The American Club Opened in 1918 as lodging for immigrant workers and reopened as a resort in 1981, with fireplaces, The Immigrant Restaurant, The Wisconsin Room and an adults-only Carriage House connected to the Kohler Waters Spa.

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Winter tip Breakfast with Santa (6 December, $82 adults, $32 children) and New Year's Eve in the village are the resort's busiest winter dates, so book rooms and tables together.

2 hr
Photograph · Starved Rock Lodge
LaSalle County, Illinois, USA

Starved Rock

Under two hours by car (about 90 miles), per Starved Rock Lodge

Starved Rock's sandstone canyons are under two hours from Chicago, with 13 miles of marked trails open all year and canyon waterfalls that can freeze into icefalls in a hard winter. The Civilian Conservation Corps lodge, with what it calls the largest fireplace in Illinois, is the base.

Do
  • Canyon trails 13 miles of marked trails, open year-round from 7 a.m. to sunset; hikers must stay on marked paths.
  • Ice climbing Permitted in LaSalle, Ottawa, Wildcat and Tonti canyons for experienced climbers with their own equipment, when conditions allow; not permitted in St. Louis Canyon.
  • Guided hikes and trolley tours Run from Starved Rock Lodge; check its events calendar for winter dates.
Stay
  • Starved Rock Lodge Built by the Civilian Conservation Corps from 1933 and opened in 1939, on the National Register of Historic Places, with a two-sided limestone fireplace in the Great Hall, 1930s lodge rooms, a hotel wing, log cabins and a pool.

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Winter tip The park office does not post icefall reports; it points visitors to the 'Starved Rock Hikers' and 'Midwest Ice Conditions' Facebook groups, so check them before driving out for frozen falls.

2 hr 30 min
Photograph · Saugatuck/Douglas Area Convention & Visitors Bureau
Allegan County, Michigan, USA

Saugatuck & Douglas

About 2 hr 30 min by car, per the Saugatuck/Douglas visitors bureauAmtrak's Pere Marquette runs daily from Chicago to Holland, which the visitors bureau says is within a 20-minute drive of Saugatuck/Douglas.

The Art Coast towns put their winter into December: a free Winterfest at the Felt Estate with more than 60 decorated trees, a 40th-year A Christmas Carol and a mile-long drive-through light show at Crane Orchards. Small inns with fireplaces make it a two-night trip for couples.

Time it for A Christmas Carol 11–20 Dec 2026

The Saugatuck Women's Club production, in its 40th year in 2026.

Do
  • Winterfest at the Felt Estate Free family afternoon with Santa and Mrs. Claus and more than 60 decorated trees, Saturday 5 December, 1 to 3 p.m.
  • Crane Orchards Drive-Through Light Show A mile-long display, open Wednesday to Sunday in December.
  • The Bottle Run Winery Tours Six- to seven-hour tours of the Fennville wine region, $225.
Stay
  • Wickwood Inn Fourteen guest rooms in a historic inn at 510 Butler Street downtown, with chef-crafted farm-to-table breakfasts; Estate Suite No. 5 has a fireplace.
  • Hotel Saugatuck Adults-only, with 17 boutique rooms, triple-sided fireplaces and in-room breakfasts and desserts, per the visitors bureau.

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Winter tip Most of the holiday program falls between 27 November and 20 December; Saugatuck is in Michigan's Eastern time zone, an hour ahead of Chicago, so allow for it on show nights.

3 hr
Photograph · Galena Country Tourism
Jo Daviess County, Illinois, USA

Galena

About 3 hours by car, per Enjoy Illinois

Galena's historic downtown is at its most atmospheric on the December night when more than 5,000 candlelit luminaries line its streets, steps and storefronts. After the holidays, Chestnut Mountain's runs above the Mississippi and Eagle Ridge's Nordic Center and spa carry a two-night stay.

Time it for Night of the Luminaria & Living Windows 12 Dec 2026

More than 5,000 candlelit luminaries along downtown Galena, with animated holiday store windows on Main Street; hosted by the Galena Downtown Business Association.

Do
  • Chestnut Mountain Resort 19 trails and a 7-acre terrain park over more than 220 acres, with a 475-foot vertical drop.
  • The Nordic Center at Eagle Ridge An ice rink open daily until 9 p.m., sledding, snowshoeing and heated igloos for up to six guests.
  • Stonedrift Spa Eagle Ridge's spa, expanded from 3,500 to more than 12,000 square feet in a standalone building beside the Inn, with a couple's room and dry salt treatments.
Stay
  • Eagle Ridge Resort & Spa Lodge rooms, courtyard rooms and villas in the 6,800-acre Galena Territory, 6 miles southeast of Galena, with the Stonedrift Spa and a Nordic Center.
  • Chestnut Mountain Resort Full-service resort on a wooded bluff above the Mississippi, about eight miles southeast of Galena, with an indoor pool, whirlpool and sauna, per Enjoy Illinois.

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Winter tip Main Street closes to parking from 1 p.m. on luminaria day; park free at Galena Recreation Park (1721 Field Street, about 220 spaces) and take the free Jo Daviess Transit shuttle.

4 hr 15 min
Photograph · Tony Webster / Wikimedia Commons (CC BY-SA 2.0)
Door Peninsula, Wisconsin, USA

Door County

About 4 hr 15 min by car to Sturgeon Bay, per Destination Door CountyDestination Door County says Door County Courier serves the Chicago airports and Door County Trolley runs transfers from Green Bay's airport.

Door County in winter is the quiet version of the summer peninsula: 300 miles of shoreline and five state parks, ice formations along the lake and a Washington Island ferry that runs with icebreakers. Fish Creek's WinterFest fills a heated tent on the Green Bay shore on the first weekend of February.

Time it for WinterFest, Fish Creek 6–7 Feb 2027

A free festival in a heated tent at Clark Park on the Green Bay shoreline, with the Stumpf Fiddle contest, games, food and live music.

Do
  • Newport State Park Candlelight Ski A candlelit trail of about 1.5 miles ending with refreshments and a bonfire; skis and snowshoes are optional.
  • Mayberry's Carriages and Sleigh Rides Horse-drawn sleigh rides through snowy orchards near Lautenbach's Market, followed by wine and cider tasting.
  • Winter guided hikes at The Ridges Sanctuary Naturalist-led hikes focused on animal tracks.
Stay
  • The White Gull Inn Fish Creek inn open all year and offering lodging since 1896, with rooms, suites and cottages, many with fireplaces and double whirlpools, and a restaurant serving candlelight dinners and fish boils.

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Winter tip Destination Door County notes that driving from the southern county line to Northport alone takes more than an hour, so stay in Fish Creek for WinterFest rather than commuting from Sturgeon Bay.

By train 5 trips

1 hr 11 min
Photograph · NPS
Northwest Indiana, USA

Indiana Dunes

About 1 hr 10 min by South Shore Line, Millennium Station to Dune Park (South Shore Line timetable)Weekend trains leave Millennium Station at 8:30 a.m. and 10:45 a.m.; Beverly Shores, a flag stop, is five minutes past Dune Park. The National Park Service puts Dune Park about a 33-minute walk from Indiana Dunes State Park.

Indiana Dunes National Park is 71 minutes from the Loop by commuter rail: more than 16,000 acres and 15 miles of Lake Michigan shore, with dunes for sledding and over 50 miles of trails for snowshoes. The park lends snowshoes free when snow allows.

Do
  • Free snowshoe loans At the Paul H. Douglas Center in Gary, weather permitting; the center is open Wednesday to Sunday, 9 a.m. to 4 p.m.
  • Sledding Allowed on the east slope of the West Beach Trails and at the Devil's Slide in Indiana Dunes State Park.
  • Cross-country skiing and snowshoeing Trails are not groomed; the park recommends a 3- to 4-inch base and posts conditions at 219-395-1882.
Stay
  • Grand Gardner Hotel A 58-room boutique hotel at 354 Jefferson Street in Valparaiso, per Indiana Dunes Tourism.
  • Spring House Inn Described by Indiana Dunes Tourism as "one part hotel, one part country retreat," on North Mineral Springs Road.

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Winter tip The park warns visitors to stay off shelf ice on Lake Michigan, which it calls extremely hazardous; view it from the beach.

1 hr 39 min
Photograph · Milwaukee Art Museum
Wisconsin, USA

Milwaukee

About 1 hr 30 min to 1 hr 40 min by Amtrak Hiawatha, Chicago Union Station to Milwaukee Downtown (Amtrak timetable)The Hiawatha runs up to eight times a day, from 6:10 a.m. to 8:05 p.m. plus an 11:25 p.m. on Fridays; the 1:05 p.m. reaches Milwaukee at 2:44 p.m., or 2:34 p.m. on Mondays and Tuesdays.

Milwaukee is the quickest Amtrak trip on this list, and from mid-November to New Year's Day downtown runs its Holiday Lights Festival, with more than half a million bulbs across Cathedral Square and Pere Marquette Park. The Milwaukee Art Museum is marking 25 years of Santiago Calatrava's Quadracci Pavilion with free events through the winter.

Time it for Milwaukee Holiday Lights Festival 19 Nov 2026 – 1 Jan 2027

More than half a million bulbs across downtown, including a forest of more than 100 decorated evergreens in Cathedral Square Park and animated snow sculptures in Pere Marquette Park.

Do
  • Milwaukee Art Museum Open Wednesday to Sunday; adults $27, with pay-what-you-wish admission on Thursdays from 4 to 8 p.m.
  • Built to Inspire: The Quadracci Pavilion at 25 Free anniversary exhibition in the Rotunda, plus a free admission day on 18 February 2027 and family programs from 19 December to 3 January.
Stay
  • The Pfister Hotel Opened in 1893 at 424 East Wisconsin Avenue, with what it calls the largest Victorian art collection of any hotel in the world, AAA Four Diamond status since 1976 and the WELL Spa + Salon.

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Winter tip The museum's Burke Brise Soleil, the moving 'wings', was listed as under maintenance in October 2026; check before planning a visit around it.

3 hr 33 min
Photograph · Wisconsin Dells Visitor & Convention Bureau
Wisconsin, USA

Wisconsin Dells

About 3 hr 35 min by Amtrak Borealis or Empire Builder, Chicago Union Station to Wisconsin Dells (Amtrak timetables)The Borealis leaves Chicago at 11:10 a.m. and reaches Wisconsin Dells at 2:43 p.m.; the Empire Builder leaves at 3:05 p.m. and arrives at 6:42 p.m. By car, Visit Wisconsin Dells puts Chicago 193 miles away.

The self-styled Waterpark Capital of the World is the family pick on this list, with indoor waterparks that run all winter and two ski hills nearby. Two Amtrak trains a day stop in the Dells, so the 193-mile drive is optional.

Do
  • Christmas Mountain Village Skiing, snowboarding and tubing, with a winter season of December to February.
  • Cascade Mountain Skiing, snowboarding and snow tubing; children 12 and under ski free with a paid adult.
  • Mirror Lake State Park Sandstone bluffs around the lake, just outside the Dells, open year-round.
Stay
  • Wilderness Resort Billed by the visitors bureau as America's largest indoor and outdoor waterpark complex: 500,000 square feet across 600 acres, four indoor waterparks and the Wild WaterDome wave pool.
  • Kalahari Resort A 125,000-square-foot indoor waterpark that the visitors bureau calls Wisconsin's largest.

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Winter tip The Amtrak station is at 100 LaCrosse Street; book a resort transfer or taxi before you travel if you are arriving without a car.

4 hr 46 min
Photograph · Mark Hermes / Explore St. Louis
Missouri, USA

St. Louis

About 4 hr 45 min to 5 hr by Amtrak Lincoln Service, Chicago Union Station to St. Louis (Amtrak timetable)Three daily Lincoln Service trains: the 7:15 a.m. arrives at 12:01 p.m., the 5:20 p.m. at 10:23 p.m. and the 7:10 p.m. at 12:09 a.m.

St. Louis is a full city weekend by rail, and in December it lights up twice: Garden Glow runs more than two million lights through the Missouri Botanical Garden, and Winterfest brings skating and igloos to Kiener Plaza downtown. In February, Soulard stages what Explore St. Louis bills as the nation's second-largest Mardi Gras.

Time it for Garden Glow 14 Nov 2026 – 2 Jan 2027

More than two million lights through the Missouri Botanical Garden, with family nights and a 21-and-over Jingle and Mingle.

Do
  • Winterfest at Kiener Plaza Skating, s'mores stations and igloos in its 11th year, 21 November 2026 to 3 January 2027; kids skate free on Fridays.
  • Soulard Mardi Gras Weeks of events in the Soulard neighborhood, with a Grand Parade billed as the largest outside New Orleans; the 2026 parade ran on 14 February and 2027 dates are not yet posted.
Stay
  • Four Seasons Hotel St. Louis 200 rooms including 24 suites on the riverfront, with views of the Mississippi and Gateway Arch National Park, an eighth-floor outdoor pool, a spa and Ramsay's Kitchen by Gordon Ramsay.
  • 21c Museum Hotel St. Louis A contemporary art museum hotel in a former YMCA downtown, with the Spanish-inspired Idol Wolf.

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Winter tip Garden Glow tickets bought on the night from 4:30 p.m. cost $2 more and are non-refundable, so book a specific night in advance.

On Not An Atlas: Icelandair Bets on St. Louis

5 hr 45 min
Photograph · Detroit Institute of Arts
Michigan, USA

Detroit

About 5 hr 45 min by Amtrak Wolverine, Chicago Union Station to Detroit (Amtrak timetable)Three daily Wolverines leave Chicago at 6:45 a.m., 2:35 p.m. and 5:50 p.m.; the morning train reaches Ann Arbor at 12:33 p.m. and Detroit at 1:30 p.m. local time (Michigan is an hour ahead of Chicago).

The Detroit Institute of Arts' Rivera Court, covered on all four walls by Diego Rivera's Detroit Industry murals of 1932 and 1933, is a National Historic Landmark and reason enough for a winter weekend. The car city's history is close by at the Ford Piquette Avenue Plant and The Henry Ford.

Time it for Detroit Auto Show 2027 dates still to be announced; Visit Detroit lists the show for 14 to 25 January at Huntington Place, the 2026 run

The North American International Auto Show at Huntington Place downtown.

Do
  • Detroit Industry murals, Rivera Court Rivera's murals cover all four walls of the museum's central court; open Tuesday to Sunday, until 9 p.m. on Fridays.
  • Ford Piquette Avenue Plant Plank floors where the first 12,000 Ford Model Ts were assembled.
  • Henry Ford Museum of American Innovation The Driving America exhibit shows more than 100 vehicles, including a 1931 Bugatti Royale Type 41.
Stay
  • Shinola Hotel A 129-room boutique hotel at 1400 Woodward Avenue in the historic Woodward shopping district, with San Morello for wood-fired Italian, per Visit Detroit.

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Winter tip The DIA is closed on Mondays and stays open until 9 p.m. on Fridays, so arrive on the Friday morning train and see Rivera Court that evening.

A short flight 4 trips

1 hr 25 min
Photograph · Kaldari / Wikimedia Commons (Public domain)
Tennessee, USA

Nashville

About 1 hr 25 min nonstop from Midway, per Southwest's average flight time

Gaylord Opryland's 43rd A Country Christmas makes Nashville a holiday trip, with ice! featuring Home Alone carved from more than two million pounds of ice and more than five million lights across the resort. Downtown, The Hermitage Hotel has been the city's grand hotel since 1910.

Time it for A Country Christmas at Gaylord Opryland 6 Nov 2026 – 2 Jan 2027

The resort's 43rd holiday season, with ice!, more than five million lights, General Jackson Showboat holiday cruises and a free light and fountain show.

Do
  • ice! featuring Home Alone Eleven walk-through scenes and five ice slides in a 17,000-square-foot hall kept at 9°F, carved by artisans from Harbin, China; parkas provided.
  • POMP, SNOW & CIRQUEumstance Holiday stage show in the Tennessee Ballroom Theater, 24 November to 31 December 2026.
  • Pinetop Outdoor village at the resort with ice tubing, bumper cars and an outdoor skating rink.
Stay
  • The Hermitage Hotel Opened on 17 September 1910 at 231 6th Avenue North, billed as the first and only five-star hotel in Tennessee, with Drusie & Darr by Jean-Georges and the original 1910 Oak Bar.

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Winter tip ice! is kept at 9°F and the resort hands out parkas, so wear warm layers underneath.

On Not An Atlas: Dolly’s Nashville Hotel Opens Its Doors · Globus and Cosmos Tell Clients to Unpack

1 hr 28 min
Photograph · Mike Madison @BumpOpera / Courtesy of Meet Minneapolis
Minnesota, USA

Minneapolis & Saint Paul

About 1 hr 30 min nonstop from Midway to MSP, per Southwest's average flight timeAmtrak's Borealis takes about 7 hr 30 min to 7 hr 50 min from Chicago to St. Paul Union Depot (Amtrak timetable). American flies O'Hare to MSP.

The Saint Paul Winter Carnival, which Visit Saint Paul calls the oldest winter festival in the United States, runs 28 January to 7 February 2027 and ends with a torchlight parade into Rice Park. Minneapolis, across the river, adds the Four Seasons and Gavin Kaysen's Mara.

Time it for Saint Paul Winter Carnival 28 Jan – 7 Feb 2027

Saint Paul's winter festival, with roots in 1886, built around ice sculpture, parades and the Vulcan legend.

Do
  • Vulcan Victory Torchlight Parade Saturday 6 February 2027, 5:15 to 7 p.m., from West 7th and Smith to Rice Park, followed by the Vulcan Overthrow on the steps of the James J. Hill Library.
  • Ice Sculpture Park, Rice Park The carnival's ice sculptures are displayed in Rice Park for the festival's run.
Stay
  • The Saint Paul Hotel Opened on 18 April 1910 as "St. Paul's Million-Dollar Hotel" at 350 Market Street, with 254 rooms after its 1982 restoration.
  • Four Seasons Hotel Minneapolis Opened in June 2022 with 222 rooms and 39 suites on floors 23 to 30, indoor and outdoor pools with whirlpools, and Mara by chef Gavin Kaysen.

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Winter tip The torchlight parade finishes at Rice Park, so book Saint Paul rather than Minneapolis for the final weekend of the carnival.

1 hr 41 min
Photograph · Destination Toronto
Ontario, Canada Passport needed

Toronto

About 1 hr 40 min nonstop from O'Hare to Billy Bishop, per Air Canada's published scheduleAir Canada's schedule shows O'Hare departures at 7:25 a.m. and 2:00 p.m. into Billy Bishop on the downtown waterfront, twice daily from 1 June 2026; Air Canada also flies O'Hare to Pearson.

Toronto is the international city break within a short flight, and Air Canada lands you at Billy Bishop on the downtown waterfront. Late winter brings Winterlicious, the city's prix-fixe season at more than 200 restaurants, and Yorkville's hotels make a good base.

Time it for Winterlicious 2027 dates still to be announced; ran 30 January to 12 February in 2026

Prix-fixe menus at more than 200 Toronto restaurants, run by the City of Toronto.

Do
  • Winterlicious The City of Toronto's three-course prix-fixe program at more than 200 restaurants.
  • DesignTO Billed as Canada's largest celebration of design; it ran 23 January to 1 February in 2026, and 2027 dates are not yet posted.
Stay
  • Four Seasons Hotel Toronto Opened in October 2012 at 60 Yorkville Avenue, with 259 rooms including 42 suites, a 30,000-square-foot spa and Café Boulud.
  • The Hazelton Hotel 77 rooms and suites at 118 Yorkville Avenue, with ONE restaurant and Spa by Valmont's saltwater pool; billed as Canada's first and only Forbes Five-Star independent boutique hotel.

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Winter tip Air Canada published these Billy Bishop times for service starting 1 June 2026, so confirm the winter schedule when booking; U.S. travelers need a passport.

On Not An Atlas: Toronto Gets Its Only Nonstop to Mumbai · The AGO Hangs Its Frames Empty

2 hr 14 min
Photograph · Paul Broussard / New Orleans & Company
Louisiana, USA

New Orleans

About 2 hr 15 min nonstop from Midway, per Southwest's average flight time

Mardi Gras falls on Tuesday 9 February 2027, and New Orleans & Company lists parades from Twelfth Night on 6 January, building to Muses, Endymion and Bacchus the weekend before. It is the warm-weather trip on this list, and the new Fairmont New Orleans opens downtown in November 2026.

Time it for Carnival season and Mardi Gras 6 Jan – 9 Feb 2027

New Orleans' Carnival season, with the Rex Organization marking 155 years since its first parade in 1872.

Do
  • Parade weekend Provisional 2027 dates: Muses on 4 February, Endymion on 6 February, Bacchus on 7 February, and Zulu and Rex on Mardi Gras Day, 9 February.
  • New Orleans Museum of Art Hanaq Pachap and Jim Hodges' Craig's Closet run through 31 March 2027, and Second Nature: Japanese Rinpa Paintings opens on 2 October 2026.
  • Allstate Sugar Bowl College Football Playoff semifinal at the Caesars Superdome on 15 January 2027.
Stay
  • Fairmont New Orleans Opening 2 November 2026 at 1010 Common Street in the Central Business District, with about 250 rooms, two restaurants led by Emeril Lagasse, a rooftop lounge and a 10,000-square-foot spa.
  • NOPSI Hotel 217 rooms in the nine-story 1927 headquarters of New Orleans Public Service Inc. at 317 Baronne Street, with a rooftop pool and bar.

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Winter tip New Orleans & Company says final 2027 routes are still to come; book rooms for the weekend of 6 and 7 February, when Endymion and Bacchus roll, as soon as you commit.

On Not An Atlas: New Orleans in 12 Plates, From Toronto · Four Road Trips Through the South

The season

The winter calendar

The dates that make a winter trip, as the organizers have announced them. Events still waiting on 2027 dates are listed with their trip, not here.

November 2026

  • 6 Nov 2026 – 2 Jan 2027A Country Christmas at Gaylord OprylandNashville
  • 14 Nov 2026 – 2 Jan 2027Garden GlowSt. Louis
  • 19 Nov 2026 – 1 Jan 2027Milwaukee Holiday Lights FestivalMilwaukee
  • 21 Nov 2026 – 3 Jan 2027Winterfest, Kiener PlazaSt. Louis

December 2026

  • 3 Dec 2026 – 28 Feb 2027Frozen FairwaysKohler
  • 11–20 Dec 2026A Christmas CarolSaugatuck & Douglas
  • 12 Dec 2026Night of the Luminaria & Living WindowsGalena

January 2027

February 2027

CPS schools close for winter vacation from 21 December 2026 to 1 January 2027, with 4 January a non-attendance day for students, and for spring vacation from 22 to 26 March 2027. Amtrak seats, Door County inns and New Orleans hotels go early for both. School holidays in Chicago →

Questions

Quick answers

What are the best weekend getaways from Chicago in winter?

Close in, Milwaukee is about 1 hr 30 min by Amtrak Hiawatha, Harbor Country about 90 minutes by car and the Indiana Dunes about 71 minutes by South Shore Line. For two nights, Kohler's American Club is about two hours north and Galena about three hours west, and Nashville and Minneapolis are each about 1 hr 30 min by air from Midway.

What is a romantic winter getaway from Chicago?

The American Club in Kohler pairs the Kohler Waters Spa with skating and snowshoeing at Frozen Fairways. In Harbor Country, the adults-only Inn at Union Pier heats its rooms with antique Swedish tile stoves; Hotel Saugatuck is adults-only with triple-sided fireplaces; and Eagle Ridge near Galena has its Stonedrift Spa and heated igloos.

Which weekend trips from Chicago work by train?

Per the published timetables: Milwaukee is about 1 hr 30 to 1 hr 40 min on the Hiawatha, the Indiana Dunes about 71 minutes on the South Shore Line, Wisconsin Dells about 3 hr 35 min, St. Louis about 4 hr 45 min on the Lincoln Service and Detroit about 5 hr 45 min on the Wolverine, which also stops in New Buffalo for Harbor Country.

Where can you ski near Chicago?

In the Lake Geneva area, The Mountain Top at Grand Geneva has 20 runs and Wilmot Mountain has 25 named runs and 11 lifts. Chestnut Mountain near Galena has 19 trails and a 475-foot vertical drop above the Mississippi, and Christmas Mountain and Cascade Mountain are near Wisconsin Dells.

Is Door County worth visiting in winter?

For a quiet trip, yes: Destination Door County lists cross-country skiing and snowshoeing, a candlelit ski at Newport State Park and Fish Creek's WinterFest on 6 and 7 February 2027. It is about 4 hr 15 min by car to Sturgeon Bay, and the White Gull Inn in Fish Creek is open all year.

When is Mardi Gras 2027?

Tuesday 9 February 2027. New Orleans & Company lists parades from 6 January, with Endymion on 6 February and Bacchus on 7 February, though final routes are still to come. Southwest's average Midway to New Orleans flight time is 2 hr 14 min.

What are the best winter getaways from Chicago by car?

The closest are Lake Geneva (1 hr), Harbor Country (1 hr 30 min), Kohler (2 hr), Starved Rock (2 hr). Times are the tourism boards' own figures from downtown in normal conditions; allow more in snow.

Do I need a passport for these trips?

Only for the trips that cross a border: Toronto. Check passport and entry rules for your nationality before booking; everything else on this list is domestic.

Sources (94)

Checked 21 October 2026. Dates change: confirm with the event or hotel before you book. Spot something out of date? Tell us via our corrections policy.

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