Plan a trip to see Montrose Dog Beach

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Pendry Chicago

Downtown Chicago

NZ$2,411

per person

23 Dec - 28 Dec

found 1 day ago

Return flight included

Auckland (AKL) to Chicago (ORD)

18.8/10 Exceptional! (1,128 reviews)

Staff was our favorite part! Very very professional and friendly

Reviewed on 14 Nov 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

NZ$3,265

per person

23 Dec - 28 Dec

found 1 day ago

Return flight included

Auckland (AKL) to Chicago (ORD)

18.8/10 Exceptional! (1,773 reviews)

It was absolutely wonderful. We were upgraded to a suite which was pretty sweet (no pun intended)! At night the surrounding view of the lake along the lakeside of the hotel was spectacular. The Rebar on the mezzanine floor with a live musician playing a saxophone on a Saturday, was a cozy and lively setting. Welcome champagne upon check in was a nice touch. The Terrace 16 restaurant/bar also served scrumptious choices on the menu. Overall, very satisfied with our stay.

Reviewed on 14 Nov 2025

Hilton Chicago O'Hare Airport

O'Hare

NZ$2,748

per person

23 Dec - 28 Dec

found 1 day ago

Return flight included

Auckland (AKL) to Chicago (ORD)

16.4/10 Exceptional! (2,152 reviews)

Clean and quiet and comfortable

Reviewed on 14 Nov 2025

Tours & day trips

See all 154 activities

Architecture River Tour

Private & custom tours

See all 48 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 25 activities

Chicago Craft Brewery Barrel Bus Tour

Free cancellation available

Attractions

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360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

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Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Montrose Beach

Soak up the sun with views of Lincoln Park and Lake Michigan at this city beach known for its fun sports and extensive amenities.

Montrose Harbor

With trails, a beach and a bird sanctuary, this spacious city harbor is a good place to sail from and a great place to hang out.

Hutchinson Street Historic District

You can learn about the history of Chicago with a visit to Hutchinson Street Historic District. Experience the entertainment choices and acclaimed theatre scene in this vibrant area.

Kathy Osterman Beach

Spend a day swimming and paddling on Lake Michigan or soaking up the sun on a peaceful beach located at the northern tip of Lincoln Park.

Puptown Dog Park

After visiting Puptown Dog Park, make a plan to see the other sights and activities in Chicago. Amble around the area's lakeside or experience its theatre scene.