South Loop Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Lobby sitting area
    Jul 17 - Jul 20

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.4/10 - Very good (1,949 reviews)
    "The outlets did not work. One elevator was out of service and the other one was too slow. Location is the only good thing"
    Reviewed May 30, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $1,168
    CA $881
    per traveller
    found 1 day ago
    Hotel Saint Clair- Magnificent Mile
  • Smart TV
    Jul 8 - Jul 12

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (490 reviews)
    "Amazing place"
    Reviewed May 26, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $1,682
    CA $1,045
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Breakfast, lunch and dinner served
    Jul 11 - Jul 18

    Fairmont Chicago at Millennium Park Gold Experience + Flight

    Downtown Chicago
    7 nights
    4.5 star property
    9.2/10 - Wonderful (142 reviews)
    Roundtrip • Toronto (YYZ) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $3,834
    CA $2,821
    per traveller
    found 1 day ago
    Fairmont Chicago at Millennium Park Gold Experience
  • Exterior
    Aug 3 - Aug 7

    Hilton Chicago + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (2,845 reviews)
    "Staff was really helpful, the view from the 19th floor was excellent"
    Reviewed May 30, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • Nonstop ORD - YUL • Nonstop
    CA $1,503
    CA $1,126
    per traveller
    found 1 day ago
    Hilton Chicago
  • Suite, 1 Bedroom, Corner | Private kitchen
    Aug 2 - Aug 8

    Homewood Suites by Hilton Chicago Downtown South Loop + Flight

    Downtown Chicago
    6 nights
    3.0 star property
    8.8/10 - Excellent (2,341 reviews)
    "Great location"
    Reviewed May 29, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $2,422
    CA $1,840
    per traveller
    found 10 hours ago
    Homewood Suites by Hilton Chicago Downtown South Loop

Where to stay in South Loop

Find the best South Loop areas and neighborhoods for the activities you enjoy most. Learn more about South Loop
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

South Loop Hotel Deals

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 CA $192 per night from Jun 29 to Jun 30
CA $192
CA $229 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,135 reviews)
"The room was small and was missing modern convinces-microwave-better seating space. The staff were friendly and the restaurant was great! I only wished we had gotten a better room! Special shout out to Steve P. the doorman for his service and friendly demeanor!!"

Reviewed on May 30, 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $330 per night from Jun 30 to Jul 1
CA $330
CA $432 total
Jun 30 - Jul 1
includes taxes & fees
8.6/10 Excellent! (2,845 reviews)
"Staff was really helpful, the view from the 19th floor was excellent"

Reviewed on May 30, 2026

Hilton Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Jul 1 to Jul 2
CA $176
CA $209 total
Jul 1 - Jul 2
includes taxes & fees
7.4/10 Good! (2,612 reviews)
"Welcoming and friendly staff"

Reviewed on May 30, 2026

Travelodge by Wyndham Downtown Chicago
See all 4,648 properties in South Loop
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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a South Loop vacation package cost?
Starting from a low , a vacation package is your passport to low-cost travel. Custom make your South Loop escape by selecting from our extensive range of hotels, flights and rental cars.
How do I get a cheap travel package to South Loop?
Creating your own South Loop vacation package with Expedia is a simple way to save. We have more than 550 airlines and 1,000,000 properties spread across the globe. With such a wonderful range to pick from, you'll have no trouble creating your next dream getaway.
Where should I stay in South Loop?
Make sightseeing a breeze by staying someplace close to South Loop's iconic attractions. McCormick Place and Millennium Park are two of the best in the area.
What are the top hotels in South Loop?
Sonder South Wabash and Hotel BnB are a couple of the most sought-after properties in South Loop. Why not take a look at the rates and facilities at each and then decide?
How far in advance should I book my South Loop vacation?
It can be tricky to know when the best time is to book your trip to South Loop. But generally the earlier you book, the more affordable the prices. In some cases, you can book your flights and hotels up to 12 months before departure. If you're hoping for a last-minute getaway, no need to worry! There are fantastic deals posted on Expedia all the time.
What does an Expedia South Loop travel package include?
That depends on what type of getaway you're thinking about. South Loop vacation deals can include hotels, car rentals and flights. You can mix and match to create the package that fits your needs. You can also add on experiences and activities after you've booked to score even bigger discounts.
What should I know before booking a South Loop travel package?
So many places to wander around, so many things to see and do. With a package, you can check more of them off your list. Combine your hotels, flights and rental cars and see how much you save.
Can I choose my airline with a South Loop Expedia vacation package?
You sure can. Expedia has access to more than 550 partner airlines worldwide, so choose the carrier that's a good fit for your needs.
If I'm not able to travel, can I cancel my South Loop vacation package?
Yes, you can cancel your South Loop booking if your travel plans have been upended. Whether you'll incur a penalty or not depends on your hotel, airline or car rental company. You may be able to change or cancel for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $55
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
See all activities in Chicago

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.