Armour Square Holidays

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Your Armour Square Holiday

From its history to its cafes and dining, there are tons of fabulous reasons to book a holiday package to Armour Square. When you want to escape the everyday, this commercial neighbourhood is calling your name. Not sure what to do and see during your trip to Armour Square? Nearby attractions such as Willis Tower, Art Institute of Chicago and University of Illinois Chicago are good places to start. Stop daydreaming and start doing. When it's time to lock in your next holiday to Armour Square, Expedia is here to help.

Price found within the past 48 hours. Click for updated prices.
  • Smart TV
    Jul 10 - Jul 14

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (488 reviews)
    "Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely."
    Reviewed May 22, 2026
    Return • Birmingham (BHX) - Chicago (ORD)
    BHX - ORD • 1 stop ORD - BHX • 1 stop
    £1,486
    £1,182
    per traveller
    found 1 hour ago
    Level Chicago Fulton Market
  • Seasonal outdoor pool, pool loungers
    Aug 2 - Aug 7

    Viceroy Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,231 reviews)
    "We had an incredible stay here. The room was very nice as we stayed in a junior suite so the extra charge was definitely worth it. You’re on the 17th floor and you’re able to have a good view of the city. You also are one floor away from the rooftop restaurant and bar. The decor and aesthetics in the hotel are top-notch. Definitely picture worthy. Definitely walkable and it’s less than quarter mile from the hotel to the lake. 10 out of 10 definitely recommend."
    Reviewed May 23, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 2 stops ORD - LHR • 2 stops
    £1,921
    £1,465
    per traveller
    found 5 hours ago
    Viceroy Chicago
  • Front of property – evening/night
    Jul 9 - Jul 14

    The Peninsula Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.8/10 - Exceptional (1,000 reviews)
    "Great stay!"
    Reviewed May 17, 2026
    Return • London (LGW) - Chicago (ORD)
    LGW - ORD • 1 stop ORD - LGW • 1 stop
    £2,506
    £1,955
    per traveller
    found 1 day ago
    The Peninsula Chicago
  • Terrace/patio
    Jul 10 - Jul 14

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,511 reviews)
    "Walls are paper thin. We literally heard snoring all night from the room next to us. Also, the smell of cigarette smoke kept coming into our room. Rooms were nice and clean. The view was 🔥."
    Reviewed May 23, 2026
    Return • Birmingham (BHX) - Chicago (ORD)
    BHX - ORD • 1 stop ORD - BHX • 1 stop
    £1,719
    £1,366
    per traveller
    found 1 hour ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Exterior detail
    Aug 2 - Aug 7

    The Emily Hotel + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,320 reviews)
    "Had a decent stay. Valet parking is ridiculously priced. Our room faced the train - so it was pretty loud in the morning. The location of the property is the best quality - lots of great bars, restaurants and shopping within walking distance. I’d stay here again - without a car."
    Reviewed May 22, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 2 stops ORD - LHR • 2 stops
    £1,791
    £1,425
    per traveller
    found 5 hours ago
    The Emily Hotel

Where to stay in Armour Square

Find the best Armour Square areas and neighborhoods for the activities you enjoy most. Learn more about Armour Square
Downtown Chicago

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Top hotels in Armour Square

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is £118 per night from 26 May to 27 May
£118
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,139 reviews)
"tiniest room i’ve ever stayed in and shower leaked all over the floor and"

Reviewed on 25 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £233 per night from 16 Jun to 17 Jun
£233
16 Jun - 17 Jun
includes taxes & fees
9.4/10 Exceptional! (4,239 reviews)
"Solo traveler. Spacious king room. Double sink bathroom. The breakfast buffett was one of the best I've had. Convenient location to Michigan Ave and Riverwalk."

Reviewed on 25 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is £107 per night from 27 May to 28 May
£107
27 May - 28 May
includes taxes & fees
7.8/10 Good! (1,467 reviews)
"Complimentary breakfast was really nice."

Reviewed on 24 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,712 properties in Armour Square
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
All Inclusive Holidays
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Family Friendly Holidays

Frequently asked questions

How much does an Armour Square travel package cost?
Starting from an incredible , you can customize your Armour Square package. Simply bundle hotels, flights and rental cars and we'll reward you with discounts.
If I'm not able to travel, can I cancel my Armour Square travel package?
It's impossible to predict what the future holds, so it's comforting to know that you can cancel or change your Armour Square travel package. If your booking was made in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal for more information.
How do I get a cheap travel package to Armour Square?
It's easy. Just bundle. Hotels, rental cars and flights — combine whatever you need into an Armour Square travel package and save. Score even better deals when you include extras such as experiences or tours to your booking. But that's not the only good part. You have the flexibility to customize your holiday your way. We offer more than 550 airlines and 1,000,000 properties worldwide, so that everyone has an opportunity to travel and fulfil those holiday fantasies.
Does Expedia offer Book Now, Pay Later Armour Square holidays?
Expedia has teamed up with online lender Klarna to make your next getaway a little easier on the wallet. Paying by instalment means you can spread the costs of your next big holiday, leaving you with more cash to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find one that works with your budget. Check out these flexible payment options:

  • Pay monthly holidays: Klarna has manageable monthly payment plans that work for all types of budgets, so you can lock in that well-earned holiday now.
  • Pay in instalments holidays: Into the idea of paying off your holiday in multiple transactions? Then check out this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than all of it upfront) makes it easier to hit that "book now" button, go for a low deposit holiday payment plan from Klarna.

Where should I stay in Armour Square?
Take the leg work out of sightseeing by staying someplace close to Armour Square's iconic attractions. Millennium Park and Wrigley Field are two visitor favourites.
What are the top hotels in Armour Square?
Hyatt Regency Chicago and The Godfrey Hotel Chicago are a couple of the most sought-after hotels in Armour Square. Why not check out the facilities and amenities at each and then make a decision?
How far in advance should I book my Armour Square holiday?
Travellers are normally able to look up international flights on Expedia within 12 months of the departure date. Booking at the last minute? With a stroke of luck, it's still possible to nab an affordable ticket only weeks before your flight.
What does an Expedia Armour Square travel package include?
With Expedia, you can choose a combination of flights, hotels and car rentals to build your ideal Armour Square package. Once you've made your booking, you can add on the fun things like tours and activities. Remember — the more you bundle, the more discounts you'll get!
What should I know before booking an Armour Square travel package?
You'll land impressive savings when you bundle your flights, hotels and rental cars into a package. Not only that, booking everything together just makes things easier. So why waste your money or time? Whether you're organising an upscale romantic escape or a budget family adventure, take a look at our package deals today.
Can I choose my airline with an Armour Square Expedia travel package?
Definitely. Expedia has over 550 airline partners to select from globally. With so much choice, finding the ideal carrier to whisk you away to Armour Square will be a cinch.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

£16
per child
98% of travellers recommend
Flyover in Chicago
See all activities in Chicago

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.