MidwestWeekends.com — Your Travel Guide to the Upper Midwest

Serious reservations

Here's a guide to the lodgings, campsites and permits you should nail down now for travel in 2018.

Canoeing in the Boundary Waters.

© 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. Planning to take the kids on a field trip to Chicago's famous museums? If you settle on Aug. 2-5, 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 23-29 — 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 St. Patrick's Day, a Saturday this year — and also for those that create long weekends. In 2018, Christmas Eve and New Year's Eve are on Mondays, creating four-day weekends for many people.

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. 

Call now if you want to attend such huge events as Apple Festival in Bayfield, Oct. 5-7, when 60,000 people cram themselves into the tiny northern Wisconsin village of 500.

In Decorah, Iowa, 75,000 people pour into town for Nordic Fest, July 26-28, and rooms are so hard to get they're practically a family heirloom. 

One of the hardest reservations to get is a room in Duluth for Grandma’s Marathon June 15-17, 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.

Waterfront hotel in Ephraim.

© Beth Gauper

For summer, book lodgings in Door County far in advance.

But 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.

There are many ploys that increase the odds of getting a reservation. It’s best to call the day after a big event, but if you have to call later and the inn is full, ask to put your name on the waiting list.

And look for new properties that haven’t been advertised much. Peruse city websites or ask the staff at visitors bureaus if there are new places to stay.

The prize rooms go to people who pay attention, ask questions — and make a lot of calls as well as checking websites.

Many people offer homes on Airbnb just for big festivals, and there are many more on vacation-rental sites. For details, see How to find a great place to stay.

Campsites and cabins 

A camper cabin at Holland State Park.

© Beth Gauper

The beachfront cabins in Michigan's Holland State Park are extremely popular.

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.

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.

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 2018 include the America's Beauty Show, 80,000 people over April 28-30; National Restaurant Association, 70,000 people over May 19-22; Lollapalooza, 300,000 people over Aug. 2-5; and the International Manufacturing Technology Show, 94,000 people over Sept. 10-15.

Art on the Square in Madison.

© Beth Gauper

Two art fairs draw more than 200,000 people to Madison in July.

The Chicago Marathon draws 45,000 people over Oct. 5-7.

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. 25-30.

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 2018

This month-by-month guide will help you nail down the most-coveted and hardest-to-get reservations.


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, 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.

Bands at the Chicago Blues Festival.

© Torsten Muller

Chicago's Blues Festival draws half a million people to the city in June.

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.

Reserve early for the best choice of entry permits into the Boundary Waters Canoe Area Wilderness. Entry permits for two Fall Lake entry points and three on Moose Lake are taken from Dec. 14 to Jan. 17 and allocated by lottery about a week later.

Others will be first-come, first-served starting Jan. 31 at Recreation. gov, 877-444-6777.

For more, see Minnesota's Boundary Waters.

In northern Minnesota's Voyageurs National Park, where motorized boats are allowed, campsites can be reserved six months in advance at Recreation.gov, 877-444-6777.

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.

Cabins in Michigan parks also are coveted and can be booked a year in advance.   Call 800-447-2757 or reserve online.

Bicycling in Chicago.

© Beth Gauper

Tourists as well as locals flock to Chicago's lakefront in summer.

Iowa also has a nice variety of well-priced rustic and modern cabins in state parks. They book a year in advance.


In 2018, Valentine’s Day falls on the Wednesday before Presidents Day weekend, so you won't have to book rooms at popular inns and B&Bs too far in advance.

Cross-country ski lodges and alpine ski resorts book up early for Presidents Day weekend, Feb. 17-19.

On Wisconsin's Chequamegon Bay, the folksy Book Across the Bay ski and snowshoe benefit race/tour, between Ashland and Washburn on Feb. 17, fills up both towns.

The American Birkebeiner between Cable and Hayward, North America’s largest cross-country ski marathon, will fill northwest Wisconsin Feb. 22-25

In Iowa, the deadline for mail entries in the cross-state bicycle tour RAGBRAI is Feb. 15, and the deadline for weeklong entries is April 1. The ride, July 22-28 in 2018, limits weeklong riders to 8,500. Entries are accepted by lottery.

Many other popular bike tours also fill up.

An apple-orchard float in Bayfield.

© Torsten Muller

The Apple Festival parade in Bayfield draws big crowds.

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 1 in 2018, 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 in July 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.

Reservations for air-conditioned lodgings at Luther open in early April; 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.

Only 5,000 tickets are sold for the Aug. 11 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 3-5, timed to coincide with the blooming of 250,000 tulips. 

In Holland, Mich., Tulip Time spreads over two weekends, May 5-13.

The annual Wright Plus Housewalk is May 19 in Oak Park, Ill., with interior tours of private homes, many designed by Frank Lloyd Wright. Tickets sell out far in advance.

Split Rock Lighthouse.

© Beth Gauper

Reservations for campsites with a view of Split Rock Lighthouse are the hardest to get in Minnesota.


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 2019, Memorial Day is May 27, 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.

In Wisconsin, some park and forest campgrounds have a high percentage of first-come, first-served sites. Arrive on Wednesdays or Thursdays to increase the odds of finding a campsite without a reservation.

All of the campsites at four state forests, Tower Hill State Park in Spring Green and the Elroy-Sparta State Trail are first-come, first-served.

Grandma’s Marathon in Duluth is June 16. Many hotels have three-night minimums, and most raise rates for the weekend. Check in February and May for cancellations.

In March, dorm rooms become available at the College of St. Scholastica, the University of Minnesota-Duluth and the University of Wisconsin-Superior; shuttles serve guests who stay there.

Costumed riders on RAGBRAI.

© Beth Gauper

Iowa's RAGBRAI and many other bike tours fill up quickly.

In Chicago, the free Blues Festival, June 8-10, draws more than half a million people, and two Old Town art fairs and Midsommerfest in the Andersonville neighborhood add to the total.

Summerfest, which Milwaukee calls “the world’s largest music festival,’’ brings nearly a million people to the lakefront festival grounds. It’s June 27-July 1 and July 3-8. 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.


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 30-July 7.

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 11-15 and draws big crowds.

Cherry pie-eating in Traverse City.

© Traverse City Tourism

Cherry pie-eating contests are part of Traverse City's National Cherry Festival.

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 14-15.

It 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.

It's also the time to reserve weekends and holidays in Minnesota state parks for next year.

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.

In Minnesota’s state parks, all of the campsites can be reserved

Duluth's Bayfront Festival Park.

© Beth Gauper

There's a festival in Duluth's Bayfront Park nearly every weekend.


The tourism behemoth in eastern Wisconsin is the annual EAA AirVenture in Oshkosh, the July 23-29 Experimental Aircraft Association festival. 

In western Minnesota lakes country, the We Fest country-music festival fills the area around Detroit Lakes, Aug. 2-4, though most festival-goers camp on the grounds.

The Bayfront Blues Festival is the biggest music weekend in Duluth, Aug. 10-12.

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. 11-12.


In Chicago, Jazz Festival draws 300,000 people over Labor Day weekend, Aug. 30-Sept. 2. In Milwaukee, Harley-Davidson is celebrating its 115th anniversary Aug. 29-Sept. 2.

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. 3.

Photographing fall colors on Oberg Mountain.

© Beth Gauper

On Minnesota's North Shore, everyone hopes to catch fall colors like these around Oberg Mountain.


In La Crosse, Oktoberfest draws crowds to the banks of the Mississippi Sept. 27-30.

Apple Festival in Bayfield fills the Wisconsin village on Lake Superior to bursting; people stay as far away as Duluth. It’s Oct. 5-7.

The Fall Art Tour in southwest Wisconsin on the third weekend of October 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. 18-21, and every room is reserved on the North Shore. Indoor water parks in the Wisconsin Dells also are popular.

Many Halloween events and ghost tours are very popular. For the ones closest to Halloween, reserve as soon as possible.

Pella street dancers.

© Beth Gauper

In May, Pella's Tulip Time brings 150,000 people to a town of 10,000.


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 Saturday.

The Lake Superior Storm Festival in Grand Marais is the same weekend, Nov. 9-11.

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. 22.

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.


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.

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.

North of Milwaukee, shop-filled Cedarburg fills up on the first weekend of December, when it holds three big arts and crafts fairs.


For more on popular events, call 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. 

Last updated on March 16, 2018