Best Flight From Sky Harbor Intl. To CHI

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Amazing PHX to CHI Flight Deals

The cheapest flights to CHI-All Airports were $140 for round trip flights and $61 for one-way flights in the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Dec 10 - Sun, Dec 13
PHX
Phoenix
ORD
Chicago
$140 Roundtrip, found 5 days ago
$140
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Dec 10 from Phoenix to Chicago, returning Sun, Dec 13, priced at $140 found 5 days ago
Sun, Dec 6 - Sat, Dec 12
PHX
Phoenix
ORD
Chicago
$147 Roundtrip, just found
$147
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Dec 6 from Phoenix to Chicago, returning Sat, Dec 12, priced at $147 just found
Thu, Dec 10 - Sun, Dec 13
PHX
Phoenix
ORD
Chicago
$151 Roundtrip, found 5 days ago
$151
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Dec 10 from Phoenix to Chicago, returning Sun, Dec 13, priced at $151 found 5 days ago
Thu, Dec 3 - Mon, Dec 7
PHX
Phoenix
ORD
Chicago
$217 Roundtrip, found 3 days ago
$217
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Dec 3 from Phoenix to Chicago, returning Mon, Dec 7, priced at $217 found 3 days ago
Tue, Dec 8 - Mon, Dec 14
PHX
Phoenix
MDW
Chicago
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Dec 8 from Phoenix to Chicago, returning Mon, Dec 14, priced at $217 found 1 day ago
Thu, Nov 19 - Sat, Nov 21
PHX
Phoenix
ORD
Chicago
$217 Roundtrip, found 21 hours ago
$217
Roundtrip
found 21 hours ago
Select United flight, departing Thu, Nov 19 from Phoenix to Chicago, returning Sat, Nov 21, priced at $217 found 21 hours ago

Hotels near CHI-All Airports Airport (CHI)

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$129 nightly
The price is $153 total per night from Nov 10 to Nov 11
$153 total
Nov 10 - Nov 11
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Opens in a new windowCongress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
$122 nightly
The price is $145 total per night from Nov 22 to Nov 23
$145 total
Nov 22 - Nov 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Opens in a new windowThe Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$116 nightly
The price is $138 total per night from Nov 23 to Nov 24
$138 total
Nov 23 - Nov 24
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Opens in a new windowRiver Hotel
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The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
$119 nightly
The price is $141 total per night from Nov 23 to Nov 24
$141 total
Nov 23 - Nov 24
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.
8.6/10 Excellent! (2,176 reviews)
"Hotel was nice. Just need more elevators"

Reviewed on Oct 27, 2026

Opens in a new windowThe Wade
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
$134 nightly
The price is $159 total per night from Nov 2 to Nov 3
$159 total
Nov 2 - Nov 3
Total with taxes and fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
8/10 Very Good! (2,481 reviews)
"The front desk lady during our check-in was not friendly nor welcoming. No greetings, no smile and sounds rude in explaining about vehicle parking. Property only has valet parking which is expensive. Breakfast room was good and kudos to one staff who was nice."

Reviewed on Oct 27, 2026

Opens in a new windowThe Chicago Hotel Collection - Magnificent Mile
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$133 nightly
The price is $158 total per night from Nov 27 to Nov 28
$158 total
Nov 27 - Nov 28
Total with taxes and fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Opens in a new windowHilton Chicago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
172 W Adams St Chicago IL
$119 nightly
The price is $141 total per night from Nov 22 to Nov 23
$141 total
Nov 22 - Nov 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
8.6/10 Excellent! (1,012 reviews)
"I booked this hotel through hotwire and experienced numerous problems. I won't go into all the issues, but trust that there were many. I want to bring attention to the fact that a front desk manager lied to me about a room refund. I contacted the front office manager and he ignored my messages. I ..."

Reviewed on Oct 27, 2026

Opens in a new windowTHE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
$212 nightly
The price is $248 total per night from Nov 22 to Nov 23
$248 total
Nov 22 - Nov 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
Opens in a new windowHilton Chicago O'Hare Airport
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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.

Top Picks

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.