Plan a trip to see Milwaukee Avenue

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Trump International Hotel & Tower Chicago

Downtown Chicago

per person

23 Sept - 26 Sept

found 1 day ago

Return flight included

London (LHR) to Chicago (ORD)

9.4/10 Exceptional! (1,659 reviews)

Excellent establishment great staff very clean and spacious

Reviewed on 5 Aug 2025

The Peninsula Chicago

Downtown Chicago

Save 100% on your flight

per person

23 Sept - 26 Sept

found 1 day ago

Return flight included

London (LHR) to Chicago (ORD)

9.8/10 Exceptional! (1,000 reviews)

Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on 26 Jul 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

per person

22 Oct - 29 Oct

found 1 day ago

Return direct flight included

London (LHR) to Chicago (ORD)

9.4/10 Exceptional! (2,049 reviews)

Amazing view, nice room sizes and very clean

Reviewed on 3 Aug 2025

Tours & day trips

See all 178 activities

Architecture River Tour

Free cancellation available

Food, drink & nightlife

See all 37 activities

Chicago: Architecture Boat Tour with Drinks

Free cancellation available

Private & custom tours

See all 34 activities

Eastside Chicago The Heist Exploration Game and Tour

Free cancellation available

Adventure & outdoor

See all 15 activities

Chicago White Sox Baseball Game at Guaranteed Rate Field

Attractions

See all 15 activities

360 CHICAGO Observation Deck

Free cancellation available

Popular places to visit

Northwestern College Chicago Campus

Walk around the campus at Northwestern College Chicago Campus during your visit to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

The Gift Theatre

You can make plans for a show at The Gift Theatre during your stay in Chicago. Discover the top-notch restaurants and entertainment choices in this vibrant area.

Copernicus Center

You can make plans for a show at Copernicus Center during your stay in Chicago. Amble around this vibrant area's lakeside or attend a sporting event.

Norwood Park Dog Park

After visiting Norwood Park Dog Park, make a plan to see the other sights and activities in Chicago.

Portage Park

After visiting Portage Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.

Six Corners

You can browse for the perfect souvenirs at Six Corners during your visit to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.