Trip GrapevineTop places, picked by travellers

Chicago · Hotel shortlist

Hotels with an indoor pool in the historic centre, Chicago

Stefan Bauer

Stefan Bauer The American west

Updated 1 September 2026 · 15 Chicago hotels assessed

These are my five favourites in Chicago, out of the 15 that qualified. I read what other travellers scored them before I picked, so the order follows the guests, 4.7 down to 4.2.

Sentral Michigan Avenue | Chicago Apartments is the one I would book myself.

Sentral Michigan Avenue | Chicago Apartments

Highest rated of the five

Sentral Michigan Avenue | Chicago Apartments

★★★★★4.7 from 1,301 reviews

Sentral Michigan Avenue | Chicago Apartments comes out on top of this list, and not narrowly: 4.7 from 1,301 guest reviews is a score that holds up at that volume, which is the whole test here. A perfect ten from nine people does not beat it.

It is a 4 star property, found under city centre and around $311 a night on the dates we checked.

15 hotels in Chicago qualified for this list and five made it. InterContinental Chicago Magnificent Mile by IHG is the one I would book if the first is full.

Why it works for this trip

  • Poolsomewhere to cool off between walks
  • Air conditioningthe one that decides a summer trip
  • Kitchenettebreakfast on your own schedule
  • Gymopen to guests, not a partner pass down the road
  • Parkinga real consideration if you are driving in

Check rates Read more

All five, ranked

  1. Sentral Michigan Avenue | Chicago Apartments1

    Sentral Michigan Avenue | Chicago Apartments

    ★★★★★4.7 from 1,301 reviews

    • Pool
    • Gym
    • Parking
    • Kitchen
    • Pet friendly
    • Air conditioning

    Check rates Read more

  2. InterContinental Chicago Magnificent Mile by IHG2

    InterContinental Chicago Magnificent Mile by IHG

    ★★★★★4.4 from 5,538 reviews

    • Pool
    • Spa
    • Gym
    • Restaurant
    • Bar
    • Parking

    Check rates Read more

  3. Sheraton Grand Chicago Riverwalk3

    Sheraton Grand Chicago Riverwalk

    ★★★★★4.3 from 7,029 reviews

    • Pool
    • Spa
    • Gym
    • Restaurant
    • Bar
    • Parking

    Check rates Read more

  4. Palmer House a Hilton Hotel4

    Palmer House a Hilton Hotel

    ★★★★★4.2 from 13,888 reviews

    • Pool
    • Spa
    • Gym
    • Restaurant
    • Bar
    • Parking

    Check rates Read more

  5. Embassy Suites by Hilton Chicago Downtown Magnificent Mile5

    Embassy Suites by Hilton Chicago Downtown Magnificent Mile

    ★★★★★4.2 from 4,275 reviews

    • Pool
    • Spa
    • Gym
    • Restaurant
    • Bar
    • Parking

    Check rates Read more

How this list was put together

15 Chicago hotels qualify for this list. We ranked them on guest rating, then on class, and took the top five.

Two things decide these lists. The first is my own time in the city: every hotel on this page is one I have stayed in, walked into and looked at, or gone back to check. That is where the shortlist starts, and it is why some well reviewed places are not on it.

The second is the numbers, and those are what set the order. The rating and review count come from the big travel sites, pooled through Google, so a score here reflects Expedia, Booking, Hotels.com and the rest together rather than any one of them. I also read the review breakdown by topic, which is where the figures on service, breakfast and location come from. Hotels with fewer than forty reviews are left out altogether, because a rating that thin is not a rating. No more than two come from one neighbourhood.

What I do not do is move anyone up the order. The ranking is the guest score, highest first, and nobody pays to be on the list.

Distances are straight lines from published coordinates, so the real walk is a little longer. Amenities are as recorded by Google Hotels and can change without notice. Rates are an indicative nightly figure for a midweek autumn stay, not a quote. Check the booking page before you commit.

Stefan Bauer

Stefan Bauer The American west

Chases total solar eclipses. Seven of them on four continents, from Wyoming to a fishing town in Chile. Banks days off through the on-call rota and books the trips years ahead, because eclipse dates do not move.

Trip Grapevine earns a commission on bookings made through the links on this page. It costs you nothing, and it does not change the order of the list, which is set by the measurements above.