Here's a guide to the lodgings, campsites and permits you should nail down now for travel in 2020.
© Lauren Gagner
The best permits for entry into the Boundary Waters go fastest.
In the Upper Midwest, travel can be competitive.
Many festivals are so big and so fun that everyone wants to go. If you do, too, you'll have to act fast to stay ahead of the crowds.
And sometimes, you also need to know when not to visit a certain area, so you can avoid sold-out hotels or sky-high rates.
Planning to take the kids on a field trip to Chicago's famous museums? If you settle on July 30-Aug. 3, when 300,000 music fans will be in town for the rock festival Lollapalooza, you won't be able to find a hotel.
If you'll be within 60 miles of Oshkosh, Wis., July 20-26 — and that includes Green Bay and the Lake Michigan shore — you'll be competing for rooms with the 300,000 people who go to EEA AirVenture.
Expect Milwaukee to be very popular — thanks to the Democratic National Convention it'll host July 13-16, many travel magazines have published stories about it, and Airbnb says it's the No. 1 "trending destination" in 2020.
The first half of January is the best time to go after hard-to-get reservations at annual festivals.
Most people rebook their lodgings as they're leaving after a big festival. But often deposits are due in January, and there’s always someone who doesn’t send one and forfeits the room. So be poised to snap it up.
The smaller the town, the harder it is to get a reservation. However, new Airbnbs are popping up all the time in small towns, and some people forget to check for them.
There are quite a few in Decorah, Iowa, where 75,000 people pour into town for Nordic Fest in July, and hotel rooms are so hard to get for that weekend that a reservation is practically a family heirloom.
It's the same thing in Bayfield, Wis., where Apple Festival on the first weekend of October brings 60,000 people into the tiny northern Wisconsin village of 500.
© Beth Gauper
For summer, book lodgings in Door County far in advance.
One of the hardest reservations to get is a room in Duluth for Grandma’s Marathon in June, when 14,700 runners and 30,000 to 40,000 spectators fill the town.
Hotels fill up the day after the previous year’s race, and, with hundreds of people calling every month, few hotels bother to keep waiting lists.
Airbnbs also fill immediately. But many have three- or six-month reservation windows, so watch for openings.
And in February, many people who reserved last June will find out they didn’t get into the race, and they’ll start to cancel. That’s the time to call hotels, as well as during the third week of May, when 30-day cancellation policies go into effect.
The best time to reserve a room for any big event is on the day after it ends on the previous year.
And look for newly opened properties that haven’t been advertised much. Ask the staff at visitors bureaus if there are — or will be — new places to stay.
For more, see How to find a great place to stay.
© Beth Gauper
The beachfront cabins in Michigan's Holland State Park are extremely popular.
Campsites and cabins
To reserve the choicest camper cabins and lodges in Minnesota, Wisconsin, Iowa and Michigan state parks, be online or at the phone a year in advance.
The best campsites in state parks also go fast. For Iowa campsites, call three months in advance; for Michigan campsites, six months in advance; for Wisconsin campsites, 11 months in advance; and Minnesota campsites, a year in advance.
For summer weekends, you’ll increase your odds if you also reserve for Thursday night; then, you can make your call a day earlier. You must use the site on Thursday, however, or you'll forfeit the entire stay.
The best time to reserve a cabin for a week at a popular lake resort, especially for a group, is a year in advance. Call the Monday after that week ends, because most — but not all — families reserve for the next year before they leave.
If you can't plan that early, look in winter or spring.
In Chicago, hotel rates depend on how much competition there is on a weekend.
The summer festivals draw a lot of people, but many are locals or day-trippers. For big conventions, however, everybody needs a hotel room.
© Beth Gauper
Tourists as well as locals flock to Chicago's lakefront in summer.
Before booking a non-refundable fare to Chicago, first check its convention calendar to see if a huge convention is in town. If so, rooms will be very expensive, if available.
Big conventions/events in 2020 include the Inspired Home Show over St. Patrick's Day, 63,000 people over March 14-17; the Beauty Show, 43,000 people over April 18-20; National Restaurant Association, 70,000 people over May 16-19; Lollapalooza, 295,000 people over July 30-Aug. 2; Information Technology Managed Services, 94,000 people over Sept. 14-19; and the Chicago Marathon, 40,000 people over Oct. 9-10.
Christmas shoppers might think the week after Thanksgiving would be a good time to visit, but 55,000 members of the Radiological Society of North America are in town Nov. 29-Dec. 4.
For more, see Where to stay in Chicago.
If you want to take Amtrak or the Megabus, book as soon as possible; the cheapest seats sell first.
Reserving for 2020
This month-by-month guide will help you nail down the most-coveted and hardest-to-get reservations.
© Beth Gauper
The Illgen Falls cabin in Minnesota's Tettegouche State Park overlooks Illgen Falls.
January is a good time to reserve for any place you want to visit this year.
In Minnesota state parks, reserve a cabin or guesthouse for next New Year’s Eve, a Thursday that will be part of a four-day weekend. In Tettegouche State Park, the four cabins on Mic Mac Lake and the Illgen Falls Cabin are in particular demand for the holidays.
Reservations for cabins, suites and guesthouses in Minnesota state parks can be made a year in advance online or at 866-857-2757, toll-free in the United States and Canada.
Lodgings in Minnesota state parks also are in demand for the long Martin Luther King weekend.
Wisconsin's state parks also have nine cabins for people with disabilities, $30. They’re very popular and can be reserved starting Jan. 10 for the following year. Reservations are taken by individual parks.
In western Minnesota, Maplelag is one of the region's best cross-country ski lodges.
Reserve early for the best choice of entry permits into the Boundary Waters Canoe Area Wilderness. Reservations can be made starting the last Wednesday in January, Jan. 29 in 2020, at Recreation. gov, 877-444-6777.
For more, see Minnesota's Boundary Waters.
In Michigan state parks, campsites can be reserved six months in advance. At some campgrounds, particularly those on the beach-lined west coast of Lake Michigan, 100 percent of sites can be reserved, so it's crucial to reserve early.
At Porcupine Mountains Wilderness State Park on the Upper Peninsula, 80 percent of sites can be reserved.
Iowa also has a nice variety of well-priced rustic and modern cabins in state parks. They book a year in advance.
© Beth Gauper
There's a festival in Duluth's Bayfront Park nearly every weekend.
In 2020, Valentine’s Day falls on the Friday before Presidents Day weekend, so many people will be reserving a long weekend at popular inns and B&Bs.
The American Birkebeiner between Cable and Hayward, North America’s largest cross-country ski marathon, will fill northwest Wisconsin Feb. 20-23.
© Beth Gauper
In May, Pella's Tulip Time brings 150,000 people to a town of 10,000.
In Iowa, campsites can be reserved three months in advance at 877-427-2757. Only 50 percent of campsites can be reserved.
Reserve early for spring-break trips to the indoor water parks of the Wisconsin Dells. The three best and biggest are the Kalahari, Great Wolf Lodge and Wilderness Resort.
The weeks before Easter, which is April 12 in 2020, are busiest.
Many other hotels around the region also have indoor water parks that children will think are plenty of fun.
Going to Chicago by train is a great spring-break trip. The cheapest seats sell first on Amtrak, so reserve as early as possible.
If you'd like to camp in a Twin Cities park reserve, especially over a holiday weekend, watch for the opening of the reservation windows in January and March.
This is the time to reserve accommodations for big summer festivals, if you haven't already.
In the northeast Iowa town of Decorah, Nordic Fest, July 25-27, draws 75,000 people to the town of 8,500. A reservation
in one of the town’s motels or B&Bs is nearly impossible to get, so
most people camp or stay in private homes or rooms at Luther College.
For reservations for air-conditioned lodgings at Luther, call 563-387-1538. Eventually, people book rooms as far away as Rochester or La Crosse.
If you want to go to the annual Great Taste of the Midwest in Madison, the second-longest running craft-beer festival in North America, you'll need to send in a mail order for tickets or show up in person the first Sunday of May at one of various vendors in Madison.
© Torsten Muller
Chicago's Blues Festival draws half a million people to the city in June.
Only 5,000 tickets are sold for the Aug. 8 event, held in Olin-Turville Park.
In May, the big festivals begin. One of the best is Tulip Time in Pella, Iowa, which brings 150,000 people to the town of 10,000. It’s May 7-9, timed to coincide with the blooming of 250,000 tulips.
In Holland, Mich., Tulip Time spreads over two weekends, May 2-10.
In Wisconsin, campsites can be reserved 11 months in advance, 888-947-2757, so now is the time to think about reserving for next year. In 2021, Memorial Day is May 31, the Fourth of July is on a Sunday and Labor Day is Sept. 6.
The most in-demand campsites are in Peninsula and Devil’s Lake state parks and the Crystal Lake and Clear Lake campgrounds of Northern Highland-American Legion State Forest near Minocqua.
Grandma’s Marathon in Duluth is June 20. Many hotels have three-night minimums, and most raise rates for the weekend. Check in February and May for cancellations.
In Chicago, the free Blues Festival, June 5-7, draws more than half a million people.
© Traverse City Tourism
Cherry pie-eating contests are part of Traverse City's National Cherry Festival.
Summerfest, which Milwaukee calls “the world’s largest music festival,’’ brings nearly a million people to the lakefront festival grounds. It’s June 24-28 and June 30-July 5. Hotels fill, but there are rooms available at the very nice dorms of Marquette University.Then there are Milwaukee's big heritage festivals, starting with PrideFest and Scottish Fest in June and ending with Indian Summer Festival the weekend after Labor Day; in between, there’s Polish Fest, Bastille Days, Festa Italiana, German Fest, Irish Fest and Mexican Fiesta.
At beach towns everywhere, weekends will be jam-packed from now through the middle of August.
The free music-and-food festival Taste of Chicago is July 8-12 and draws big crowds.
© Beth Gauper
Two art fairs draw more than 200,000 people to Madison in July.
In Madison, the Art Fair on the Square and Art Fair Off the Square draw more than 200,000 people to the Capitol/State Street/Monona Terrace area. They're July 11-12.
In eastern Wisconsin, the EEA AirVenture July 20-26 fills up so many hotel rooms it may even affect people doing the Lake Michigan Circle Tour, on which stops in beach towns should be reserved far in advance.
Another big event on Lake Michigan is the Democratic National Convention, which will bring 50,000 people to Milwaukee July 13-16.
This is the time to start looking for a lake resort for next year, though some resorts have last-minute cancellations. If possible, drop by resorts in person while traveling in the area this summer.
It's also the time to reserve weekends and holidays in Minnesota state parks for next year.
© Beth Gauper
Reservations for campsites with a view of Split Rock Lighthouse are the hardest to get in Minnesota.
which has a very scenic location on the North Shore but not many sites,
is the hardest-to-get camping reservation, followed by Temperance River,
Tettegouche, Itasca, Gooseberry Falls, McCarthy Beach (on the Iron
Range, near Hibbing), Bear Head Lake (near Ely), Judge C.R. Magney, Jay
Cooke and Cascade River.
In Minnesota’s state parks, all of the campsites can be reserved.
In the far northeast corner of Minnesota, it's notoriously hard to find close-in rooms for the Grand Portage Rendezvous and Powwow, when re-enactors from across the continent converge on Grand Portage National Monument. Reserve right after this year's event, Aug. 7-9.
In northeast Iowa, the Yankees will play the Chicago White Sox at the Field of Dreams movie site in Dyersville, near Dubuque, on Aug. 13.
In Duluth, the Bayfront Blues Festival is the biggest of many music weekends, Aug. 14-16.
© Beth Gauper
Labor Day is the only day people can walk on the Mackinac Bridge.
In Chicago, Jazz Festival draws 300,000 people over Labor Day weekend, Aug. 29-Sept. 6.
The Labor Day Bridge Walk over the Mackinac Bridge, the third-longest suspension bridge in the world, fills lodgings within a 50- to 100-mile radius of St. Ignace and Mackinaw City, Mich., and especially Mackinac Island. It's Sept. 7.
© Beth Gauper
On Minnesota's North Shore, everyone hopes to catch fall colors like these around Oberg Mountain.
The Fall Art Tour in southwest Wisconsin Oct. 16-18 has become extremely popular, with many devoted customers returning year after year. Artists open their studios in and around Mineral Point, Spring Green and Baraboo, with shoppers taking in the fall scenery between stops.
Accommodations for fall in Door County are in high demand. Leaf color stays beautiful through the third week of October.
Because of the Education Minnesota teacher conference, Minnesota schoolchildren have a four-day weekend Oct. 15-18, and every room is reserved on the North Shore. Indoor water parks in the Wisconsin Dells also are popular.
This is a quiet month for festivals, but not on stormy Lake Superior. This year, the annual beacon-lighting at Split Rock Lighthouse on Minnesota's North Shore, commemorating the Nov. 10 loss of the crew of the Edmund Fitzgerald, is on a Tuesday.
© Torsten Muller
The Apple Festival parade in Bayfield draws big crowds.
The Lake Superior Storm Festival in Grand Marais is on the closest weekend.
Many people like to reserve a cabin or villa on Minnesota's North Shore to watch the gales of November or fix Thanksgiving dinner Nov. 26.
Holiday festivities get going in earnest the weekend after Thanksgiving; see Great holiday festivals.
Hard-core shoppers should go the first weekend of December so they also can hit the annual One of a Kind fine-arts sale at the Merchandise Mart.
Last updated on January 16, 2020