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Chicago & Milwaukee route inspiration

Chicago & Milwaukee

German markets, lit avenues and lakefront rinks

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5 days through Chicago, Milwaukee.

Chicago & Milwaukee is a 5-day curated route with 2 destinations and 17 places to eat, see, and do. Preview stops and timing, then plan it in TripsCircle.

  1. 1
    Chicago on the Chicago & Milwaukee route

    Destination 01

    Chicago

    9 places

    Three nights for the market, the Mag Mile lights and the rinks.

    • Christkindlmarket near ChicagoPhoto: DR04 · CC BY 3.0

      Christkindlmarket

      German-style Christmas market in Daley Plaza since 1996, with wooden stalls, ornaments, bratwurst and Glühwein.

      Tip Weekday evenings are calmer; there is a second location in Wrigleyville.

      ShopThe Loop$1.5 hrAfter dark

    • Magnificent Mile

      Michigan Avenue's shopping stretch north of the river, with about a million lights strung through its trees in winter.

      Tip Walk north from the river to the Water Tower after dark, then warm up in one of the hotel lobbies.

      SeeNear North SideFree1.5 hrAfter dark
    • Lincoln Park Zoo ZooLights near ChicagoPhoto: Christine Zenino · CC BY 2.0

      Lincoln Park Zoo ZooLights

      The city's free zoo turns into a light show with millions of bulbs from late November to early January.

      Tip Book a timed ZooLights entry for weekend nights; weekdays are quieter.

      DoLincoln Park$1.5 hrAfter dark
    • McCormick Tribune Ice Rink near ChicagoPhoto: Adam Jones · CC BY 2.0

      McCormick Tribune Ice Rink

      Free outdoor rink in Millennium Park next to Cloud Gate, open from mid-November into March; skate rental extra.

      Tip The city's Christmas tree stands in Millennium Park nearby.

      DoMillennium Park$60 minEvening
    • Maggie Daley Park Skating Ribbon near ChicagoPhoto: Alanscottwalker · CC BY-SA 4.0

      Maggie Daley Park Skating Ribbon

      A quarter-mile loop of ice winding over the hills of Maggie Daley Park, with the skyline rising behind it.

      Tip Reserve a skate time online on weekends.

      DoGrant Park$60 minEvening
    • The Walnut Room at Macy's near ChicagoPhoto: Ken Lund · CC BY-SA 2.0

      The Walnut Room at Macy's

      Marshall Field's 1907 dining room on State Street, where a Great Tree rises through the room each Christmas.

      Tip Reservations go fast for December; the State Street holiday windows are on the way in.

      EatThe Loop$$75 minLunch

    • The Berghoff

      German restaurant on West Adams Street since 1898, with schnitzel, sauerbraten and its own root beer and lager.

      Tip The bar holds Chicago's first liquor license issued after Prohibition.

      EatThe Loop$$75 minDinner
    • Goodman Theatre near ChicagoPhoto: ajay_suresh · CC BY 2.0

      Goodman Theatre

      Chicago's oldest nonprofit theater, staging A Christmas Carol every holiday season since 1978.

      Tip Book by early November for weekend shows.

      DoThe Loop$$$2.5 hrEvening
    • The Drake near ChicagoPhoto: w_lemay · CC BY-SA 2.0

      The Drake

      1920 lakefront hotel at the top of the Magnificent Mile, known for afternoon tea in the Palm Court.

      Tip Holiday teas in the Palm Court book up weeks ahead.

      StayStreeterville$$$60 min
  2. 2
    Milwaukee on the Chicago & Milwaukee route

    Destination 02

    Milwaukee

    8 places

    Two nights for the downtown lights, a mansion Christmas and beer halls.

    • Cathedral Square Park near MilwaukeePhoto: Michael Barera · CC BY-SA 4.0

      Cathedral Square Park

      Downtown park at the center of the Milwaukee Holiday Lights Festival, filled with lit trees and displays.

      Tip The festival also lights Pere Marquette Park and Red Arrow Park; walk between all three after dark.

      SeeEast TownFree45 minAfter dark
    • Pabst Mansion near MilwaukeePhoto: Michael Barera · CC BY-SA 4.0

      Pabst Mansion

      Captain Frederick Pabst's 1892 Flemish Renaissance mansion, decorated room by room for its Christmas tours.

      Tip Holiday tours run late November through December and sell out on weekends.

      SeeMarquette$$75 minAfternoon
    • Milwaukee Art Museum near MilwaukeePhoto: Michael Barera · CC BY-SA 4.0

      Milwaukee Art Museum

      Lakefront museum whose Calatrava-designed Quadracci Pavilion opens and closes its steel wings each day.

      Tip Watch the wings open at 10am or close at 5pm from the footbridge.

      SeeLakefront$$2 hrMorning
    • Milwaukee Riverwalk near MilwaukeePhoto: Michael Barera · CC BY-SA 4.0

      Milwaukee Riverwalk

      Three miles of path along the Milwaukee River through downtown and the Third Ward, quiet and icy in winter.

      OutdoorsDowntownFree60 minMorning
    • Milwaukee Public Market near MilwaukeePhoto: Michael Barera · CC BY-SA 4.0

      Milwaukee Public Market

      Indoor food hall in the Historic Third Ward with seafood, cheese, chocolate and a wine bar.

      Tip The St. Paul Fish Company counter is the classic lunch stop.

      ShopHistoric Third Ward$60 minLunch
    • Mader's near MilwaukeePhoto: Michael Barera · CC BY-SA 4.0

      Mader's

      German restaurant on Old World Third Street since 1902, with schnitzel, pork shank and steins of German beer.

      Tip The dining rooms are dressed for Christmas through December.

      EatWestown$$1.5 hrDinner
    • Lakefront Brewery near MilwaukeePhoto: Michael Barera · CC BY-SA 4.0

      Lakefront Brewery

      Riverside craft brewery known for its comedic tours and a beer hall with a Friday fish fry and polka.

      Tip Brewery tours sell out on winter weekends; book online.

      DrinkBrewers Hill$1.5 hrFriday night
    • The Pfister Hotel near MilwaukeePhoto: Michael Barera · CC BY-SA 4.0

      The Pfister Hotel

      Milwaukee's grand 1893 hotel, with a painted-ceiling lobby that holds a towering Christmas tree each December.

      StayEast Town$$$60 min

The moments that shape this trip.

Planning Chicago & Milwaukee.

Spend three nights in Chicago: mulled wine and wooden stalls at Christkindlmarket in Daley Plaza, the lit trees of the Magnificent Mile, ZooLights at Lincoln Park Zoo and a skate under the skyline at Millennium Park and Maggie Daley Park. Add the Great Tree in Macy's Walnut Room, German food at The Berghoff and the Goodman Theatre's A Christmas Carol. Then take the train 90 minutes north to Milwaukee for two nights of the Holiday Lights Festival in Cathedral Square, the Pabst Mansion dressed for Christmas, the Calatrava wings of the Milwaukee Art Museum over a frozen lakefront, and schnitzel at Mader's.

Good for City lovers who want classic big-city Christmas, German-American food and an easy train hop.

When to go

Chicago's Christkindlmarket opens the Friday before Thanksgiving and runs to December 24. The Magnificent Mile Lights Festival parade is the Saturday before Thanksgiving, and the lights stay up into January. ZooLights runs most evenings from late November to early January. The McCormick Tribune Ice Rink and the Maggie Daley Park Skating Ribbon open in mid-November. Milwaukee's Holiday Lights Festival starts the week before Thanksgiving and stays lit through New Year's Day. Expect highs around freezing and wind off the lake.

Getting around

Fly into Chicago O'Hare (ORD) or Midway (MDW); both have L train service downtown. Amtrak's Hiawatha runs several times a day between Chicago Union Station and Milwaukee Intermodal Station in about 90 minutes, so no car is needed. In Chicago, the L and buses cover everything on this route; in Milwaukee, the free Hop streetcar links downtown, the Third Ward and the lakefront.

Tips for your crew

  • Christkindlmarket sells a new collectible mug each year; your first mulled wine includes it, and refills cost less.
  • Go to Christkindlmarket and the Magnificent Mile on a weekday evening; weekend afternoons in December are packed.
  • Bring skates or rent early in the evening; both downtown Chicago rinks close for ice resurfacing and run timed sessions on busy nights.

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