Serious reservations
Here's a guide to the lodgings, campsites and permits you should nail down early.
© Beth Gauper
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 early August, 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., in late July — 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.
And always book early for holidays that fall on weekends — such as the Fourth of July and Halloween, both on Thursday in 2024 — and also for those that create long weekends.
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 full weekend of October brings 60,000 people into the tiny northern Wisconsin village of 500.
© Beth Gauper
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 check as soon as their window opens.
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.
© Torsten Muller
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 120 days to a year in advance.
The best campsites in state parks also go fast. For Minnesota campsites, 120 days in advance; Iowa campsites, call three months in advance; for Michigan campsites, six months in advance; and for Wisconsin campsites, 11 months 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.
Popular destinations
Reserve as early as you can for summer weekends in beach towns on Lake Michigan and Milwaukee and summer and fall weekends in Duluth and Door County.
It's the same for fall weekends at North Shore cabins in Minnesota and inns along the Mississippi River.
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.
© Lauren Gagner
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.
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 then.
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 2024
This month-by-month guide will help you nail down the most-coveted and hardest-to-get reservations.
© Beth Gauper
JANUARY
January is a good time to reserve for any place you want to visit this year.
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.
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 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.
© Beth Gauper
Cabins in Michigan parks also are coveted and can be booked a year in advance. Call 800-447-2757 or reserve online.
Iowa also has a nice variety of well-priced rustic and modern cabins in state parks. They book a year in advance.
FEBRUARY
On Feb. 6, the University of Minnesota-Duluth begins taking reservations for dorm rooms and apartments for Grandma's Marathon. The College of St. Scholastica also rents dorm rooms, with reservations starting March 1.
Cross-country ski lodges and alpine ski resorts book up early for Presidents Day weekend.
On Wisconsin's Chequamegon Bay, the folksy Book Across the Bay ski and snowshoe benefit race/tour, between Ashland and Washburn on President's Day weekend fills up both towns.
© Beth Gauper
The 50th American Birkebeiner between Cable and Hayward, North America's largest cross-country ski marathon, will fill northwest Wisconsin with 35,000 spectators watching 13,500 skiers Feb. 21-25.
In Iowa, campsites can be reserved three months in advance at 877-427-2757. Only 50 percent of campsites can be reserved.
In Minnesota, campsites can be reserved 120 days in advance.
Split Rock, 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.
MARCH
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 March 31 in 2024, 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.
APRIL
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.
© Torsten Muller
MAY
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.
Only 5,000 tickets are sold for the Aug. 10 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 2--4, timed to coincide with the blooming of 250,000 tulips.
In Holland, Mich., Tulip Time spreads over two weekends, May 4-12.
The annual Wright Plus Housewalk is May 18 in Oak Park, Ill., with interior tours of private homes, many designed by Frank Lloyd Wright. Tickets sell out far in advance.
© Beth Gauper
JUNE
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 2024, Memorial Day is May 26, the Fourth of July is on a Thursday and Labor Day is Sept. 2.
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 22. Many hotels have three-night minimums, and nearly all raise rates for the weekend. Check in February and May for cancellations.
In Chicago, the free Blues Festival June 6-9 draws more than half a million people.
Summerfest, which Milwaukee calls "the world's largest music festival," brings nearly a million people to the lakefront festival grounds. It's June 20-22, June 28-30 and July 4-6. Hotels fill, but there are rooms available at the very nice dorms of Marquette University.
© Traverse City Tourism
Then there are Milwaukee's big heritage festivals, starting with PrideFest and Polish Fest in June and continuing with Bastille Days, German Fest, Irish Fest, Mexican Fiesta and the Wisconsin Highland Games on Labor Day weekend.
JULY
The Fourth of July is busy everywhere. It will be especially busy in Traverse City on Lake Michigan, where 500,000 people come for National Cherry Festival June 29-July 6.
At beach towns everywhere, weekends will be jam-packed from now through the middle of August.
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 13-14.
© Beth Gauper
In eastern Wisconsin, the EEA AirVenture July 22-28 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.
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.
AUGUST
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. It's Aug. 9-11 in 2024.
In Duluth, the Bayfront Blues Festival is the biggest of many big music weekends, Aug. 9-11.
© Beth Gauper
SEPTEMBER
On Sept. 1, reserve a cabin or guesthouse in Minnesota state parks for New Year's Eve, a Tuesday. 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 120 days 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 in January.
In Chicago, Jazz Festival draws 300,000 people over Labor Day weekend.
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. 2.
The next week, the free music-and-food festival Taste of Chicago Sept. 6-8 in Grant Park draws big crowds.
In La Crosse, Oktoberfest draws crowds to the banks of the Mississippi Sept. 26-28.
OCTOBER
Apple Festival in Bayfield fills the Wisconsin village on Lake Superior to bursting; people stay as far away as Duluth. It's Oct. 4-6.
© Beth Gauper
The Fall Art Tour in southwest Wisconsin Oct. 18-20 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.
Reserve as soon as possible for fall-color weekends on the North Shore. For peak inland color, aim for the last weekend of September; for peak color along the shore, the first weekend in October.
Because of the Education Minnesota teacher conference, Minnesota schoolchildren have a four-day weekend Oct. 17-20, and every room is reserved on the North Shore. Indoor water parks in the Wisconsin Dells also are popular.
Halloween events and ghost tours book up early, especially the weekend before. Our pick for a great Halloween getaway: Chicago, which adores the holiday; be sure to bring a costume.
NOVEMBER
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 Wednesday.
© Beth Gauper
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. 28.
For some of our favorites, see 20 perfect cabins. For information about rentals, see Renting a vacation house.
Holiday festivities get going in earnest the weekend after Thanksgiving; see Great holiday festivals.
DECEMBER
This is the month to shop. Chicago is full of holiday shoppers, many of whom come for the open-air Christkindlmarket in Daley Plaza, which starts on Thanksgiving and runs through Christmas Eve. There's also a Christkindlmarket in Wrigleyville.
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 *Dec. 5-8.
Information
For more on popular events, call or sign up for newsletters from the Minnesota Office of Tourism at 651-296-5029, 800-657-3700, and the Wisconsin Department of Tourism at 800-432-8747.
For Iowa, call 800-345-4692. For Michigan, call 800-543-2937. For Illinois, call 800-226-6632.