Plan a trip to see Oak Street Beach

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The Drake

Downtown Chicago

AU$808

per person

16 Nov - 19 Nov

found 1 day ago

Return flight included

Greensboro (GSO) to Chicago (ORD)

8.8/10 Excellent! (1,291 reviews)

Great location and wonderful staff. Stayed with my family of four and we were able to easily get to all the wonderful sites we wanted to visit. The historic charm and lastige spaces enhanced our stay and our breakfast was superb.

Reviewed on 14 Oct 2025

Park Hyatt Chicago

Downtown Chicago

Save 100% on your flight

AU$1,358

per person

16 Nov - 19 Nov

found 1 day ago

Return flight included

Raleigh (RDU) to Chicago (ORD)

9.6/10 Exceptional! (1,002 reviews)

The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better.

Reviewed on 14 Oct 2025

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

AU$1,417

per person

16 Nov - 19 Nov

found 1 day ago

Return flight included

Greensboro (GSO) to Chicago (ORD)

9.4/10 Exceptional! (1,716 reviews)

Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel.

Reviewed on 15 Oct 2025

Tours & day trips

See all 164 activities

Architecture River Tour

Free cancellation available

Private & custom tours

See all 31 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 17 activities

360 CHICAGO Observation Deck

Free cancellation available

Adventure & outdoor

See all 14 activities

Chicago: Two Flight Indoor Skydiving Experience

Free cancellation available

Popular places to visit

Oak Street

During your trip to Chicago, you can find the perfect gifts to bring home at Oak Street. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.

900 North Michigan Shops

You can browse for the perfect souvenirs at 900 North Michigan Shops during your trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.

875 North Michigan Avenue

4.5/5(36 reviews)

You can find out about the history of Chicago when you stop by 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its fascinating museums.

Fourth Presbyterian Church

Fourth Presbyterian Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Water Tower Place

4.5/5(16 reviews)

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

Chicago Water Tower

4.5/5(18 reviews)

You can learn about the history of Chicago with a visit to Chicago Water Tower. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.