Plan a trip to see Chicago Shakespeare Theater

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Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

NZ$3,085

per person

29 Oct - 5 Nov

found 5 hours ago

Return flight included

Wellington (WLG) to Chicago (ORD)

9.4/10 Exceptional! (2,087 reviews)

Staff was amazing!! Everything was so easy checking in and checking out. The stay was great! It was so nice having the pier to ourselves after hours.

Reviewed on 20 Aug. 2025

The Langham, Chicago

Downtown Chicago

NZ$4,323

per person

29 Oct - 5 Nov

found 5 hours ago

Return flight included

Wellington (WLG) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on 12 Aug. 2025

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

NZ$3,126

per person

29 Oct - 5 Nov

found 5 hours ago

Return flight included

Wellington (WLG) to Chicago (ORD)

9.4/10 Exceptional! (3,344 reviews)

I enjoyed the total experience of staying at this facility.

Reviewed on 22 Aug. 2025

Tours & day trips

See all 172 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 35 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 32 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Attractions

See all 15 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 14 activities

Chicago White Sox Baseball Game at Guaranteed Rate Field

Popular places to visit

Navy Pier

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Chicago Children's Museum

You can take time to visit Chicago Children's Museum during your travels to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.

Ohio Street Beach

Why not spend a care-free afternoon at Ohio Street Beach during your travels in Chicago? Discover the acclaimed art galleries and notable monuments in this vibrant area.

Milton Lee Olive Park

Explore the great outdoors at Milton Lee Olive Park, a lovely green space in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Chicago Harbor Lighthouse

Learn about the local history of Chicago with a stop at Chicago Harbor Lighthouse. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

Smith Museum of Stained Glass Windows

You can spend an afternoon studying the exhibits at Smith Museum of Stained Glass Windows in Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.