Plan a trip to see Chicago Shakespeare Theater

Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago

Downtown Chicago

￥216,056

per person

Nov 28 - Nov 30

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (2,427 reviews)

Location is excellent, roof top bonus and breakfast double plus.

Reviewed on Oct 8, 2025

The Westin Michigan Avenue Chicago

Downtown Chicago

￥248,616

per person

Dec 25 - Dec 30

found 9 hours ago

Roundtrip non-stop flight included

Tokyo (NRT) to Chicago (ORD)

8.8/10 Excellent! (1,046 reviews)

One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.

Reviewed on Oct 2, 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

￥253,332

per person

Nov 28 - Nov 30

found 1 day ago

Roundtrip non-stop flight included

Tokyo (TYO) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.

Reviewed on Oct 6, 2025

Browse tours and tickets to explore Chicago Shakespeare Theater

Tours & day trips

See all 163 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 30 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Food, drink & nightlife

See all 27 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Attractions

See all 16 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 13 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

#architecture #navypier #facade #chicago #chitown #illinois #midwest #greatlakes #centennialwheel #travelbug #wayfarer #gadabout #nomad #wanderlust

Chicago Children's Museum

4.5/5(196 reviews)

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 theater scene.

Coast/Streeterville neighborhood hot spots offers clean beach, amenities and spectacular view of the Chicago skyline

Ohio Street Beach

Why not spend a carefree afternoon at Ohio Street Beach during your travels in Chicago? Discover the fascinating museums and notable monuments in this vibrant area.

Great place to take a break and watch sunset on a fall evening.

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 theater scene.

Wonderful #weekend getaway. Mercury tour cruise.

Chicago Harbor Lighthouse

Learn about the local history of Chicago when you spend time 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 exploring the galleries in Smith Museum of Stained Glass Windows during your trip to Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.